original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,103,277 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([CH3:22])[C:13]([C:23](OC)=[O:24])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][... | COC(=O)c1cn(S(=O)(=O)c2ccc(F)cc2)c(-c2ccccc2)c1C | null | null | CC(C)C[Al+]CC(C)C | Cl | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | -78 | 0.5 | Under a nitrogen atmosphere, a solution (40 mL) of methyl 1-[(4-fluorophenyl)sulfonyl]-4-methyl-5-phenyl-1H-pyrrole-3-carboxylate (1.48 g) in tetrahydrofuran was cooled to −78° C., and a 1.5 mol/L solution (7.9 mL) of diisobutylaluminum hydride in toluene was added dropwise over 15 min, and the mixture was further stir... | Cc1c(C=O)cn(S(=O)(=O)c2ccc(F)cc2)c1-c1ccccc1 | null | 53 | null |
1,742,368 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [F:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][CH2:8][CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:20][S:21]([N:24]1[CH2:29][CH2:28][CH:27]([O:30][C:31]2[CH:32]=[CH:33][C:34]([S:37](Cl)(=[O:39])=[O:38])=[N:35][CH:36]=2)[CH2:26][CH2:25]1)(=[O:23])=[O:22]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2... | CC(C)CNCc1ccc(F)cc1 | CS(=O)(=O)N1CCC(Oc2ccc(S(=O)(=O)Cl)nc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 18 | A solution of (4-fluorobenzyl)-isobutylamine (53 mg, 0.295 mmol) and pyridine (34 μL, 0.423 mmol) in DCM (3 mL) was treated with 5-(1-methanesulfonyl-piperidin-4-yloxy)-pyridine-2-sulfonyl chloride (75 mg, 0.211 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with DCM, washed with 1 M aqueou... | CC(C)CN(Cc1ccc(F)cc1)S(=O)(=O)c1ccc(OC2CCN(S(C)(=O)=O)CC2)cn1 | null | 37 | null |
999,371 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]=O)[C@H:10]([C:15]([CH3:23])([CH3:22])[O:16][SiH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([NH2:28])[CH:25]([CH3:27])[CH3:26].CC#N.O.CC#N>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:28][CH2:24][CH:25]([CH3:27])[CH... | CC(C)CN | CC(C)(C)OC(=O)N1C[C@@H](C=O)[C@H](C(C)(C)O[SiH2]C(C)(C)C)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared as described above for Example 9/step F (Scheme 5) from (3S*,4S*)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester and isobutylamine. MS (LC-MS): 401.1 [M+H]+; tR (HPLC, Waters Symmetry C18 column, 20-95% CH3CN/H2O/3.5 min, 95% CH3CN/H2O, 2 ... | CC(C)CNC[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]1C(C)(C)O[SiH2]C(C)(C)C | null | null | null |
795,372 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([N:10]([CH2:12][C:13]([OH:15])=O)[CH3:11])(=[O:9])=[O:8])=[CH:3][CH:2]=1.Cl.Cl.C[O:20][C:21](=[O:31])[C@H:22]([CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[NH2:23]>>[C:1]1([CH3:16])[CH:2]=[CH:3][C:4]([S:7]([N:10]([CH2:12][C:13]([NH:23][C@H:22]([C:21]([OH:31])=[O:20])[CH... | Cc1ccc(S(=O)(=O)N(C)CC(=O)O)cc1 | COC(=O)[C@@H](N)Cc1ccncc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | N-(Toluene-4-sulfonyl)sarcosine was coupled to 3-(4-pyridyl)alanine methyl ester dihydrochloride using the procedure described in Method 3 to give N-(toluene-4-sulfonyl)sarcosyl-β-(4-pyridyl)alanine. | Cc1ccc(S(=O)(=O)N(C)CC(=O)N[C@@H](Cc2ccncc2)C(=O)O)cc1 | null | null | null |
1,161,845 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[CH:18]=[C:17]([C:19]3[C:20]([C:26]([F:29])([F:28])[F:27])=[N+:21]([O-:25])[CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:14]2[CH:18]=[C:17]([C:19]3[C:20]([C:26]([F:27])([F:29])[F:28])=[N+:21]([O-:2... | COc1cc(-c2cc(-c3ccc[n+]([O-])c3C(F)(F)F)on2)cc([N+](=O)[O-])c1OC | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 18 | 3-(3-(3,4-dimethoxy-5-nitrophenyl)isoxazol-5-yl)-2-(trifluoromethyl)pyridine 1-oxide (0.81 g, 2 mmol) was taken up in dichloromethane (15 mL) and the yellowish suspension was cooled to −78° C. under argon whereupon boron tribromide (4.5 g, 18 mmol) was added dropwise. The reddish reaction mixture was allowed to warm to... | O=[N+]([O-])c1cc(-c2cc(-c3ccc[n+]([O-])c3C(F)(F)F)on2)cc(O)c1O | null | null | null |
685,845 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([Cl:15])=[CH:10][C:9]=1[NH2:16])(C)(C)C.C(O[C:23](=[O:39])[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][N:30]=[C:29]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)[CH:28]=1)=O)(C)(C)C>>[N:30]1[CH:31]=[CH:32][C:27]([C:25]2[CH2:24][C:23](=[O:39])[NH:16][C:9]3[CH:10]=[C:11]([Cl:1... | Cc1cc(NC(=O)OC(C)(C)C)c(N)cc1Cl | CC(C)(C)OC(=O)CC(=O)c1ccnc(-c2cccnc2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (2-amino-4-chloro-5-methyl-phenyl)-carbamic acid tert-butyl ester (Example J22) (102 mg, 0.4 mmol) and 3-[2,3′]bipyridinyl-4-yl-3-oxo-propionic acid tert-butyl ester (Example K57) (119 mg, 0.4 mmol) according to the general procedure M and subsequent treatment of the crude product a... | Cc1cc2c(cc1Cl)NC(=O)CC(c1ccnc(-c3cccnc3)c1)=N2 | null | null | null |
1,562,325 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:7].[CH:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](O)=[O:25])=[CH:19][CH:18]=1)([CH3:16])[CH3:15].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:7][C... | CC(C)c1ccc(CC(=O)O)cc1 | NC(c1ccccc1)c1ncco1 | null | On1nnc2cccnc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | The crude 1-(1,3-oxazol-2-yl)-1-phenylmethanamine (0.10 g, 0.57 mmol) was mixed with 4-isopropylpheylacetic acid (0.10 g, 0.57 mmol), HOAt (0.086 g, 0.63 mmol) and EDC (0.12 g, 0.63 mmol) in DMF (1.0 mL) and stirred at room temperature for 0.5 h. Purification by reverse-phase HPLC gave the product (0.025 g, 13%). ES-MS... | CC(C)c1ccc(CC(=O)NC(c2ccccc2)c2ncco2)cc1 | null | 13.1 | null |
419,214 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C=O)C>[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[CH2:12][CH2:13][N:14]([CH2:28][C:27]2[CH:30... | C1=C(c2cc3ccccc3s2)CCNC1 | Clc1ccc(CBr)cc1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | 4-(Benzothiophen-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (250 mg, 0.99 mmol) was dissolved in DMF (5 ml), potassium carbonate (412 mg, 2.9 mmol) added, and the reaction mixture stirred at room temperature for 10 minutes. 4-Chlorobenzyl bromide (306 mg, 1.5 mmol) was added and the resulting reaction mixture stirr... | Clc1ccc(CN2CC=C(c3cc4ccccc4s3)CC2)cc1 | null | 17.8 | null |
1,125,340 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2]>CCOC(C)=O.CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[NH2:10])[CH3:2] | CCCN1CCN(c2ccc([N+](=O)[O-])c(OCC)c2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 8 | 1-[3-(Ethyloxy)-4-nitrophenyl]-4-propylpiperazine (0.422 g, 1.44 mmol) was placed in a 40 mL high vial and dissolved in 10 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (0.28 g, 0.072 mmol) was added followed quickly by a screw cap septum. The vial was evacuated and filled with N2 six times to remove any ox... | CCCN1CCN(c2ccc(N)c(OCC)c2)CC1 | null | 77.8 | null |
144,949 | ord_dataset-d6cdba90760a47779a36ece5962905eb | null | 1986-01-01T00:06:00 | true | [CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)=[CH2:2].[K+].Cl[CH2:14][C:15]([O:17][CH3:18])=[O:16]>CS(C)=O>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([S:9]([CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:11])=[O:10])=[CH:7][CH:8]=1)=[CH2:2] | C=Cc1ccc(S(=O)[O-])cc1 | COC(=O)CCl | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 50 | null | To 188 ml of dimethyl sulfoxide was added 54.2 g of potassium p-vinylbenzenesulfinate, and the resulting mixture was stirred while heating at 50° C. Then, 23.0 ml of methyl chloroacetate was added dropwise to the mixture over 1 hour while maintaining it at 50° C., and the resulting mixture was stirred for 1 hour while ... | C=Cc1ccc(S(=O)(=O)CC(=O)OC)cc1 | null | null | null |
310,699 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | [F:1][C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3([CH3:27])[O:26][CH2:25][CH2:24][O:23]3)=[CH:18][CH:17]=2)[CH:5]=[C:6]([C:8]2([O:13][CH3:14])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:7]=1.[F:28][C:29]([F:36])([F:35])[C:30](OCC)=[O:31]>>[F:1][C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3([CH3:... | CCOC(=O)C(F)(F)F | COC1(c2cc(F)cc(Sc3ccc(C4(C)OCCO4)cc3)c2)CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using an analogous procedure to that described in the third paragraph of the portion of Example 5 which is concerned with the preparation of starting materials, 3-{5-fluoro-3-[4-(2-methyl-1,3-dioxolan-2-yl)phenylthio]phenyl}-3-methoxypyrrolidine was reacted with ethyl trifluoroacetate to give 3-{5-fluoro-3-[4-(2-methyl... | COC1(c2cc(F)cc(Sc3ccc(C4(C)OCCO4)cc3)c2)CCN(C(=O)C(F)(F)F)C1 | null | 58 | null |
1,481,792 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | C(OC(=O)[NH:7][C:8]1[N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:18]=2)[N:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:13]([C:11]1[CH:12]=[C:8]([NH2:7])[N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]3[CH2:24][CH2:25][O:26]... | CC(C)(C)OC(=O)Nc1cc(C(C)(C)C)nn1-c1cccc(N2CCOCC2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | A solution of Intermediate 23c (290 mg, 0.725 mmol) and TFA (3 mL) in DCM (4 mL) was stirred at RT for 1 h. The reaction mixture was applied to an SCX-2 cartridge (10 g) and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave the title compound (190 mg, 86%). LCMS (Method 1): Rt 2.... | CC(C)(C)c1cc(N)n(-c2cccc(N3CCOCC3)c2)n1 | null | 87.2 | null |
1,665,364 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [F:1][C:2]1([F:35])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:34])=[C:15]([NH:17][C:18]([C:20]4[N:24]5[CH:25]=[C:26]([CH2:29][CH2:30][C:31](=[O:33])[CH3:32])[CH:27]=[CH:28][C:23]5=[N:22][CH:21]=4)=[O:19])[CH:16]=3)[N:7]=2)[CH2:3]1.[CH3:36][Mg]Br>C1COCC1>[F:35][C:2]1([F:1])[CH2:5][CH:4]([C:6... | CC(=O)CCc1ccc2ncc(C(=O)Nc3cc(-c4noc(C5CC(F)(F)C5)n4)ccc3C)n2c1 | C[Mg]Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a stirring solution of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-carboxamide (F53) (40 mg, 0.083 mmol) in anhydrous THF (2 mL) at −78° C. under a stream of Argon was added methylmagnesium bromide (83 uL, 0.25 mmol). The reaction was stirred to room ... | Cc1ccc(-c2noc(C3CC(F)(F)C3)n2)cc1NC(=O)c1cnc2ccc(CCC(C)(C)O)cn12 | null | null | null |
1,540,501 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl.[NH:9]1[CH2:12][CH:11]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:15]=3[N:14]=2)[CH2:10]1.Cl[C:24]1[C:29]([CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[N:28][CH:27]=[CH:26][N:25]=1>CC(N(C)C)=O>[Cl:22][C:20]1[CH:19]=[CH:18][C:16]2[NH:17][C:13]([CH:11]3[CH2:12][N:9... | Clc1nccnc1C1CCOCC1 | Clc1ccc2[nH]c(C3CNC3)nc2c1 | null | Cl | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of cesium carbonate (0.82 g, 2.52 mmol), 2-(azetidin-3-yl)-5-chloro-1H-benzo[d]imidazole dihydrochloride (as described in Preparation 5) (0.18 gg, 0.63 mmol), and 2-chloro-3-(tetrahydro-2H-pyran-4-yl)pyrazine (0.13 g, 0.63 mmol) in DMA (1 mL) was heated to 80° C. for 20 h, then cooled to RT. The resulting sus... | Clc1ccc2[nH]c(C3CN(c4nccnc4C4CCOCC4)C3)nc2c1 | null | null | null |
1,140,841 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | C(OC(=O)[NH:7][C:8]1(/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=3)=[C:20]([C:35]([F:38])([F:37])[F:36])[CH:19]=2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.[ClH:40]>C(O)C>[ClH:40].[NH2:7][C:8](/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][... | CC(C)(C)OC(=O)NC1(/C=C/c2ccc(OCCCc3cccc(Br)c3)c(C(F)(F)F)c2)COC(C)(C)OC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 80 | 1 | Compound 197-1 (290 mg) was dissolved in ethanol (15 ml), concentrated hydrochloric acid (1.5 ml) was added, and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was concentrated, and the residue was washed with diethyl ether to give the object product (200 mg) as a white powder. | NC(/C=C/c1ccc(OCCCc2cccc(Br)c2)c(C(F)(F)F)c1)(CO)CO | null | null | null |
491,670 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | C([S:4][C@H:5]1[CH2:9][C@@H:8]([CH2:10][C:11]2[S:15][C:14]3=[CH:16][N:17]=[CH:18][N:13]3[C:12]=2[CH3:19])[N:7]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH2:6]1)(=O)C.C1(OP(O[C:43]2[C@H:44]([CH3:60])[C@@H:45]3[C@@H:55]([C@H:56]([OH:58])[CH3:57])[C:54](=[O:59])[N:46]3[C:47]=2[C:48]([O:50][CH2:51][CH:52]=[CH2:53])=[... | C=CCOC(=O)N1C[C@@H](SC(C)=O)C[C@H]1Cc1sc2cncn2c1C | C=CCOC(=O)C1=C(OP(=O)(Oc2ccccc2)Oc2ccccc2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The procedure of Example 23-a) is repeated to prepare 362.4 mg of a mercaptan compound as a yellow oil from 474.5 mg of (3S,5S)-3-acetylthio-1-allyloxycarbonyl-5-(3-methylimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine described in Synthesis Example 10. Allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(3-methylimidazo[5,1-... | C=CCOC(=O)C1=C(S[C@H]2C[C@@H](Cc3sc4cncn4c3C)N(C(=O)OCC=C)C2)[C@H](C)[C@@H]2[C@@H]([C@@H](C)O)C(=O)N12 | null | 40 | null |
488,491 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | CO[C:3]1O[C:5](OC)=[CH:6][CH:7]=1.[NH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:29]([F:32])([F:31])[F:30])=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19]2.C1(C)C=CC=CC=1>C(O)(=O)C>[CH3:23][N:21]1[C:22]2[C:18](=[C:17]([C:29]([F:32])([F:30])[F:31])[CH:16]=[CH:15][C:14... | COc1ccc(OC)o1 | CCOC(=O)c1cc2c(C(F)(F)F)ccc(OCCN)c2n1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 70 | 4 | After 1.28 g (9.69 mmol) of 2,5-dimethoxyfuran was added to a solution of 2.91 g (8.81 mmol) of ethyl 7-(2-aminoethoxy)-1-methyl-4-trifluoromethyl-2-indolecarboxylate in 30 ml of acetic acid, the mixture was stirred at 50° C. for 4 hours and at 70° C. for further an hour. Toluene was added to the reaction mixture follo... | CCOC(=O)c1cc2c(C(F)(F)F)ccc(OCCn3cccc3)c2n1C | null | 58.5 | null |
367,764 | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | null | 1997-01-01T00:06:00 | true | [C:1]1([N:7]2[C:11](=O)[CH2:10][C:9]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11](=[S:29])[CH2:10][C:9]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[N:8]2)[CH:6]=[CH:... | Cc1ccc(C2=NN(c3ccccc3)C(=O)C2)cc1 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5.6 g (20 mmol) of 1-phenyl-3-(4-methylphenyl)-4, 5-dihydropyrazol-5-one, 6.1 g (15 mmol) of Lawesson's reagent and 50 ml of toluene was heated under reflux for 2 hours. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1 (v/... | Cc1ccc(C2=NN(c3ccccc3)C(=S)C2)cc1 | null | 147.7 | null |
375,701 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH:20]=[C:21]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[C:22]#[N:23])[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>CO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12... | N#CC(=Cc1cc2cccnc2n(-c2cccc([N+](=O)[O-])c2)c1=O)c1cccnc1 | null | null | [Fe] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 50 | null | 0.5 g of 3-[1,2-dihydro-1-(3-nitrophenyl)-2-oxo-1,8-naphthyridin-3-yl]-2-(3-pyridyl)prop-2-enenitrile, prepared in Example 111, is suspended in 15 ml of methanol and 10 ml of water, in the presence of 0.5 g of iron powder. The suspension is heated to about 50° C. and 0.5 ml of concentrated hydrochloric acid is added dr... | N#CC(=Cc1cc2cccnc2n(-c2cccc(N)c2)c1=O)c1cccnc1 | null | 43.3 | null |
205,952 | ord_dataset-72fffaae67c8473fb9d951cb1b026646 | null | 1990-01-01T00:03:00 | true | [C:1]([C:4]1[C:13]2[C:7]([CH:8]=[CH:9][C:10]([CH:14]([CH3:16])[CH3:15])=[CH:11][CH:12]=2)=[C:6]([CH2:17][CH3:18])[CH:5]=1)([OH:3])=[O:2].[C:19](Cl)(=O)[C:20](Cl)=O.C(O)C>C1C=CC=CC=1>[CH2:19]([O:2][C:1]([C:4]1[C:13]2[C:7]([CH:8]=[CH:9][C:10]([CH:14]([CH3:15])[CH3:16])=[CH:11][CH:12]=2)=[C:6]([CH2:17][CH3:18])[CH:5]=1)=[... | CCc1cc(C(=O)O)c2ccc(C(C)C)ccc1-2 | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | CCO | null | null | null | null | null | null | null | null | null | 25 | 3 | The above-mentioned azulene carboxylic acid (3) (4.84 g, 0.002 mole) is suspended in benzene (100 ml), and oxalyl chloride (2.8 g, 0.02 mole) is added dropwise thereto under cooling with ice. The mixture is stirred for 3 hours at room temperature and cooled with ice again. Ethyl alcohol (100 ml) is added dropwise there... | CCOC(=O)c1cc(CC)c2ccc(C(C)C)ccc1-2 | null | null | null |
928,083 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13]CC)=O)=[CH:6][CH:5]=1.[H][H].Cl>C1(C)C=CC=CC=1.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([Br:3])=[CH:9][CH:8]=2)=[CH:6][CH:5]=1 | [H][H] | CCOC(=O)Cc1ccc(Br)cc1 | null | Cl | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 50 | null | To a slurry of sodium hydride (9.17 grams, 0.23 mole) in 50 milliliters of toluene was added dropwise, a solution of ethyl 4-bromophenylacetate (50 grams, 0.21 mole) in toluene (50 milliliters) at 30-32° C. After addition was completed, the reaction mixture was slowly warmed to 50° C. where the reaction began to rapidl... | O=C(Cc1ccc(Br)cc1)Cc1ccc(Br)cc1 | null | 80.7 | null |
890,220 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | Cl[C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1.[Cl:15][C:16]1[CH:28]=[CH:27][C:19]([CH2:20][N:21]2[CH2:25][CH2:24][C@@H:23]([NH2:26])[CH2:22]2)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]2[CH2:25][CH2:24][C@@H:23](... | CCOC(=O)/C=C/c1cnc(Cl)cn1 | N[C@@H]1CCN(Cc2ccc(Cl)cc2)C1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 100 | 3 | To a solution of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (1.78 g) and (3R)-1-(4-chlorobenzyl)-3-pyrrolidinamine (2.65 g) in DMF (25 mL) was added K2CO3 (5.79 g). After stirring for 3 hours at 100° C., the reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with H2O, dried ov... | CCOC(=O)/C=C/c1cnc(N[C@@H]2CCN(Cc3ccc(Cl)cc3)C2)cn1 | null | 48.8 | null |
1,190,187 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])[CH3:19]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16... | CC(C)c1ccc(S(=O)(=O)Cl)cc1 | CC(C)(C)OC(=O)NCCc1ccc(N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 0 | 16 | To a solution of [2-(4-amino-phenyl)-ethyl]-carbamicacid tert-butyl ester (10.75 g, 45.49 mmol) in pyridine (125 ml) at 0° C. 4-isopropyl-benzenesulfonyl chloride (10.45 g, 47.76 mmol) was added. The mixture was stirred at 0° C. for 1 h and 16 h at room temperature. After concentration in vacuo the residue was partitio... | CC(C)c1ccc(S(=O)(=O)Nc2ccc(CCNC(=O)OC(C)(C)C)cc2)cc1 | null | 109.3 | null |
902,569 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | ClC1C=C(C=CC=1Cl)C([NH:7][CH:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:9]1)=O.[CH3:30][O:31][C:32]1[CH:40]=[C:39]([N+:41]([O-:43])=[O:42])[CH:38]=[CH:37][C:33]=1[C:34]([OH:36])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2... | O=C(NC1N=C(c2ccccc2)c2ccccc2NC1=O)c1ccc(Cl)c(Cl)c1 | COc1cc([N+](=O)[O-])ccc1C(=O)O | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 20 | 18 | A mixture of Intermediate 3 (40 mg), 2-methoxy-4-nitro-benzoic acid (47 mg), triethylamine (0.07 ml) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (121 mg) in dry tetrahydrofuran (3 ml) was stirred at 20° C. for 18 h under a nitrogen atmosphere. The mixture was then partitioned between potass... | COc1cc([N+](=O)[O-])ccc1C(=O)NC1N=C(c2ccccc2)c2ccccc2NC1=O | null | null | null |
171,026 | ord_dataset-41558b7e18dd41999311b1762e0e13a3 | null | 1988-01-01T00:04:00 | true | CO[C:3]1[C:4]([CH2:14][C:15]#[N:16])=[C:5]([CH2:11][C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[BrH:17].[C:18]([OH:21])(=O)C>>[BrH:17].[CH3:18][O:21][C:7]1[C:8]([O:9][CH3:10])=[CH:3][C:4]2[CH2:14][C:15]([NH2:16])=[N:13][C:12]([Br:17])=[CH:11][C:5]=2[CH:6]=1 | CC(=O)O | COc1ccc(CC#N)c(CC#N)c1OC | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 3 | Here, 3,4-dimethoxy-o-phenylene-diacetonitrile (3.7 g, 0.017 mol) is suspended in glacial acetic acid (10 ml) and mixed with 30% hydrobromic acid (12 ml) in glacial acetic acid at 20° C. The mixture is stirred for 3 hours at ambient temperature, the precipitate is suction filtered, washed with glacial acetic acid and t... | COc1cc2c(cc1OC)CC(N)=NC(Br)=C2 | null | null | null |
125,369 | ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833 | null | 1985-01-01T00:01:00 | true | C(OC(C[N:12]1[C:16](=[O:17])[C@@H:15]2[C@H:13]1[CH2:14]2)=O)C1C=CC=CC=1.[C:18](=[O:21])(O)[O-:19].[Na+:22]>O1CCCC1.[Pd]>[C@@H:13]12[CH2:14][C@@H:15]1[C:16](=[O:17])[N:12]2[C:18]([O-:19])=[O:21].[Na+:22] | O=C(CN1C(=O)[C@H]2C[C@H]21)OCc1ccccc1 | O=C([O-])O | null | [Pd] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1 | A mixture of (1R,4S)-2-benzyloxycarbonylmethyl-2-azabicyclo[2,1,0]pentan-3-one (21 mg, 0.091 mmol), 10% Pd/C (10 mg) and sodium bicarbonate (7.6 mg, 0.91 mmol) in tetrahydrofuran (3 ml) water (1 ml) was hydrogenated at 40 psi on the Parr shaker for 1 hr. The mixture was then filtered and the solid residue was washed wi... | O=C([O-])N1C(=O)[C@H]2C[C@H]21 | null | null | null |
974,291 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:28]>O1CCOCC1>[ClH:28].[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:15][CH:16]=1)[C:22]1[CH:27]=... | CC(C)(C)OC(=O)N1CCN(c2ccc(OCc3ccccc3)cc2)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | The title compound (260 mg, 89.1%) was prepared from the compound from step 1 (300 mg, 0.82 mmol) and 4N HCl in dioxane by the procedure described in step 1 of Example 4: MS (ESI) m/z 269 (M+H); 1H NMR (500 MHz, DMSO-d6) δ 3.22 (br, 8H), 5.04 (s, 2H). 6.94 (br, 4H), 7.30-7.43 (m, 5H), 9.00 (br, 2H). | c1ccc(COc2ccc(N3CCNCC3)cc2)cc1 | null | 89.1 | null |
640,871 | ord_dataset-1c0bae7388cf460091d56129e95b3145 | null | 2004-01-01T00:06:00 | true | C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[C:9]2[O:13][CH:12]=[CH:11][C:10]=12)=O.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[OH:2][CH2:3][C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[C:8]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:7][CH:6]=1 | COC(=O)c1ccc(NS(C)(=O)=O)c2occc12 | null | null | CC(C)C[Al+]CC(C)C | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of 7-methanesulfonylamino-benzofuran-4-carboxylic acid methyl ester (6.42 g, 23.8 mmole) in anhydrous tetrahydrofuran (155 mL) was added a solution of diisobutylaluminum hydride (1.5M solution in toluene, 80 mL, 120 mmole) slowly at 0° C. under nitrogen. The ice bath was removed and the reaction mixture w... | CS(=O)(=O)Nc1ccc(CO)c2ccoc12 | null | 98.2 | null |
3,433 | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | null | 1976-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:18]([CH3:21])[C:19]#[N:20]>CC(C)=O>[Cl:1][C:2]1[CH:9]=[C:6]([C:5]([O:10][CH:18]([C:19]#[N:20])[CH3:21])=[CH:4][CH:3]=1)[CH:7]=[O:8] | O=Cc1cc(Cl)ccc1O | CC(Cl)C#N | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-chlorosalicylaldehyde (78 g., 0.5 mole), finely powdered anhydrous potassium carbonate (103.5 g., 0.75 mole) and acetone (500 ml.) is stirred under reflux and 2-chloropropionitrile (33.6 g., 0.375 mole) is added over a period of about 5 minutes. The mixture is heated under reflux for 1.5 hours and then t... | CC(C#N)Oc1ccc(Cl)cc1C=O | null | null | null |
922,015 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([N+:15]([O-])=O)[CH:9]=1)(C)(C)C.[S:19]1[CH:23]=[C:22]([C:24](O)=O)[N:21]=[CH:20]1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C)C=O>[S:19]1[CH:23]=[C:22]([C:24]2[NH:15][C:10]3[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][C:... | CC(C)(C)OC(=O)Nc1ccc(N)c([N+](=O)[O-])c1 | O=C(O)c1cscn1 | null | F[P-](F)(F)(F)(F)F | c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 3 | A solution of (4-Amino-3-nitro-phenyl)-carbamic acid tert-butyl ester (1-3, 0.409 g, 1.832 mmol), thiazole 4-carboxylic acid (0.226 g, 1.832 mmol) and diisopropylethylamine (0.81 mL, 4.03 mmol) in N,N-dimethylformamide (10 mL) was reacted at the ambient temperature with benzotriazol-1-yloxytripyrrolidinophosphonium hex... | Nc1ccc2nc(-c3cscn3)[nH]c2c1 | null | null | null |
103,045 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | [CH:1]1[C:14]2[CH2:13][C@H:12]3[NH:15][CH2:16][CH2:17][C@:6]4([C@H:11]3[CH2:10][CH2:9][CH2:8][CH2:7]4)[C:5]=2[CH:4]=[C:3]([C:18](=[O:20])[CH3:19])[CH:2]=1.C(N(CC)CC)C.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[C:18]([C:3]1[CH:2]=[CH:1][C:14]2[CH2:13][C@H:12]3[N:15]([C:34]([CH2:33][C:29]4[O:... | CC(=O)c1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3 | O=C(Cl)Cc1ccco1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | null | To a mixture of 1.5 g, (-)-1-(morphinan-3-yl)ethanone, 1.7 g of triethylamine and 15 ml of methylene chloride at ice-bath temperature was added a solution of 1.3 g of 2-furyl acetyl chloride in 10 ml of methylene chloride over a period of 1 hour. After the mixture had been refluxed for 4 hours, it was cooled to room te... | CC(=O)c1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C(=O)Cc1ccco1)CC3 | null | 90 | null |
1,276,382 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[C:13][Si](C)(C)C)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]#[CH:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8] | COC(=O)c1cc(Cl)ccc1C#C[Si](C)(C)C | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of methyl 5-chloro-2-[2-(trimethylsilyl)ethynyl]benzoate (10 g, 37.5 mmol) in Methanol (150 ml) was added K2CO3 (10.36 g, 75 mmol) at room temperature and in air. The reaction mixture was stirred for 1 hour before being concentrated under reduced pressure. The residue was dissolved in deionized water (50 ... | C#Cc1ccc(Cl)cc1C(=O)OC | null | 78.8 | null |
868,266 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | CN(C)[CH:3]=[CH:4][C:5]([C:7]1[N:14]2[C:10]([O:11][CH:12]=[CH:13]2)=[N:9][C:8]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=O.Cl.[NH2:24][C:25]([NH:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1)=[NH:26].[O-]CC.[Na+]>C(O)C>[F:21][C:18]1[CH:17]=[CH:... | CC(C)(C)OC(=O)N1CCC(NC(=N)N)CC1 | CN(C)C=CC(=O)c1c(-c2ccc(F)cc2)nc2occn12 | null | CC[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-(dimethylamino)-1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]prop-2-en-1-one (4.24 g, 14.2 mmol) and tert-butyl 4-{[amino(imino)methyl]amino}-piperidine-1-carboxylate hydrochloride (5.92 g, 21.2 mmol) was diluted with 40 ml of absolute ethanol and treated with 1.35 eq. of a 21% w/w solution of sod... | CC(C)(C)OC(=O)N1CCC(Nc2nccc(-c3c(-c4ccc(F)cc4)nc4occn34)n2)CC1 | null | 65.3 | null |
323,850 | ord_dataset-24ad29d930104afea313b6c3bd11099e | null | 1996-01-01T00:01:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([CH2:15][CH3:16])[N:13]=[CH:14][C:3]=12.[CH:17]1([CH2:23][NH2:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CS(C)=O>[CH2:15]([N:12]1[C:4]2=[N:5][C:6]3[C:11]([C:2]([NH:24][CH2:23][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[C:3]2[CH:14]=[N:13]1... | CCn1ncc2c(Cl)c3ccccc3nc21 | NCC1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | 48 | To a mixture of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]quinoline (10 g, 0.043 mol) and DMSO (75 ml) was added cyclohexanemethylamine (10.75 g, 0.095 mol). The reaction mixture was refluxed for about four hours, then was allowed to stand for about 2 days. About 40-50 ml of the DMSO was removed in vacuo and the residue was p... | CCn1ncc2c(NCC3CCCCC3)c3ccccc3nc21 | null | 90.5 | null |
834,728 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:20][O:21][CH2:22][CH2:23][NH2:24]>>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:19]=[CH:18][C:15]([CH2:16][NH:24][CH2:23][CH2:22][O:21][CH3:20])=[CH:14][CH:13]=2)=[O:11])[... | CC(C)N1CCN(C(=O)c2ccc(C=O)cc2)CC1 | COCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from the product of Example 15 and (2-methoxy-ethyl)-amine. | COCCNCc1ccc(C(=O)N2CCN(C(C)C)CC2)cc1 | null | null | null |
1,766,433 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | N[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:13].N([O-])=O.[Na+]>O>[CH3:11][C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:13])[C:7]=1[N+:8]([O-:10])=[O:9] | Cc1ccnc(N)c1[N+](=O)[O-] | O=S(=O)(O)O | null | O=N[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 0 | 2 | 2-Amino-4-methyl-3-nitropyridine (120 g, 0.78 mol) was suspended in water (1.6 L), a concentrated sulfuric acid (120 mL) was added dropwise, and the clear yellow solution was cooled to 0° C. in an ice bath. Sodium nitrite (98 g, 1.42 mol) dissolved in water (250 mL) was added slowly bellow the liquid surface of the rea... | Cc1cc[nH]c(=O)c1[N+](=O)[O-] | null | 91.6 | null |
1,663,408 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Br:1][C:2]1[C:3]([N:18]2[CH2:23][CH2:22][C:21]([O:25][CH3:26])([CH3:24])[CH2:20][CH2:19]2)=[C:4]([C@H:10]([OH:17])[C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[C:5]([CH3:9])=[N:6][C:7]=1[CH3:8]>C(Cl)Cl>[Br:1][C:2]1[C:3]([N:18]2[CH2:23][CH2:22][C:21]([O:25][CH3:26])([CH3:24])[CH2:20][CH2:19]2)=[C:4]([C@H:10]([O:17][C... | COC1(C)CCN(c2c(Br)c(C)nc(C)c2[C@H](O)C(=O)OC(C)C)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 48 | The isobutylene gas was bubbled into a nitrogen purged, cooled (0° C.) solution of (S)-isopropyl 2-(5-bromo-4-(4-methoxy-4-methylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-hydroxyacetate (1.45 g, 3.38 mmol) and 0.32 mL of 70% HClO4 in DCM (30 mL) for 20 min. The reaction mixture was allowed to warm to rt and stirred f... | COC1(C)CCN(c2c(Br)c(C)nc(C)c2[C@H](OC(C)(C)C)C(=O)OC(C)C)CC1 | null | 164.6 | null |
1,084,430 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | C[O:2][C:3](=[O:48])[CH:4]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:25]=1)[O:5][P:6]([C@@H:9]([NH:13][S:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:16])=[O:15])... | COC(=O)C(OP(=O)(O)[C@@H](NS(=O)(=O)Cc1ccccc1)C(C)C)c1cccc(NC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)c1 | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | 6 | To a slurry of 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1R)-(1-(benzylsulfonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid methyl ester (0.53 mmol) in 6 mL of methanol and 3 mL of H2O was added LiOH (124.3 mg, 5.3 mmol). After stirring for 6 hours, the solution was acidified to pH 2 with con... | CC(C)[C@H](NS(=O)(=O)Cc1ccccc1)P(=O)(O)OC(C(=O)O)c1cccc(NC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)c1 | null | null | null |
1,037,797 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [NH2:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[S:11](=[O:20])(=[O:19])[N:10]=2)=[C:5]([OH:21])[C:4]2[S:22][CH:23]=[CH:24][C:3]1=2.[CH3:25][C:26]([CH3:30])=[CH:27][CH:28]=O>CN(C)C(=O)C>[O:19]=[S:11]1(=[O:20])[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[NH:14][C:9]([C:6]2[C:7]... | Nn1c(=O)c(C2=NS(=O)(=O)c3ccccc3N2)c(O)c2sccc21 | CC(C)=CC=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 25 | null | The product of Example 268D (0.10 g, 0.27 mmol) was reacted with 3-methylbut-2-enal (0.5 g, 5.9 mmol) in N,N-dimethylacetamide (3 mL) in a sealed tube at 130° C. for 40 minutes in a microwave reactor. The reaction was cooled to 25° C. and concentrated under vacuum. The resulting residue was triturated with diethyl ethe... | CC(C)=CC=Nn1c(=O)c(C2=NS(=O)(=O)c3ccccc3N2)c(O)c2sccc21 | null | 80.4 | null |
788,187 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1>CN(C=O)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([S:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:12][CH:13]=1)([O-:19])=[O:18] | Sc1ccccn1 | O=[N+]([O-])c1ccc(F)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.25 | 2-mercaptopyridine (10 g) was dissolved in DMF (100 ml), 60% sodium hydride (3.6 g) was added to the mixture at 0° C., and then, the mixture was stirred for 15 minutes at room temperature. 4-fluoronitrobenzene (9.75 g) was added dropwise to the mixture at 0° C. and the mixture was stirred for 1 hour at room temperature... | O=[N+]([O-])c1ccc(Sc2ccccn2)cc1 | null | 78.5 | null |
1,152,368 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[N:20]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[C@:19]([CH2:35][OH:36])([C:31]([O:33][CH3:34])=[O:32])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1.N1C=CN=C1.[Si:42](Cl)([C:45]([CH3:48])([CH3:47])[CH... | COC(=O)[C@]1(CO)CC[C@H](c2ccc(OCc3ccccc3F)cc2)N1C(=O)OCc1ccccc1 | CC(C)(C)[Si](C)(C)Cl | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 36 | To a solution of 2-methyl 1-(phenylmethyl) (2R,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-1,2-pyrrolidinedicarboxylate (D71, 200 mg, 0.4 mmol) and imidazole (60 mg, 0.88 mmol) in dry DMF (1 ml) was added tert-butyl dimethylsilyl chloride and the mixture was stirred for 36 hours. The reaction was qu... | COC(=O)[C@]1(CO[Si](C)(C)C(C)(C)C)CC[C@H](c2ccc(OCc3ccccc3F)cc2)N1C(=O)OCc1ccccc1 | null | 74 | null |
1,168,651 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]S([O-])(=O)=O)=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:5][CH:4]=1.[C-]#[N:37].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]... | [C-]#N | COc1ccc(-c2c(-c3ccccc3)oc3ncnc(NCCCCCCCS(=O)(=O)[O-])c23)cc1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | Stir a mixture of 400 mg (approx. 0.80 mmol) 6-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]-pyrimidin-4-yl]amino}hexyl-methanesulphonate and 526 mg (8.1 mmol) potassium cyanide in 20 ml DMF overnight at 80° C. After cooling, dilute with ethyl acetate and wash with water and saturated sodium chloride solution. Dry the orga... | COc1ccc(-c2c(-c3ccccc3)oc3ncnc(NCCCCCCC#N)c23)cc1 | null | null | null |
695,573 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [CH2:1]([C:3]1[C:4](=[O:19])[NH:5][C:6](=[O:18])[NH:7][C:8]=1[O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[CH:11]=1)[CH3:2].[F:20][C:21]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:22]=1[CH2:23]Br>>[F:20][C:21]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:22]=1[CH2:23][N:7]1[C:8]([O:9][C:10]2[CH:11]=[C:12]([CH3:1... | CCc1c(Oc2cc(C)cc(C)c2)[nH]c(=O)[nH]c1=O | Fc1ccc(F)c(CBr)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (185 mg, yield: 47.9%). | CCc1c(Oc2cc(C)cc(C)c2)n(Cc2cc(F)ccc2F)c(=O)[nH]c1=O | null | 47.9 | null |
1,764,019 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]1[C:22](OC)=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[BH4-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19]... | COC(=O)C1CN(C(=O)OC(C)(C)C)CCC1O[Si](C)(C)C(C)(C)C | null | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | [BH4-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of 1-tert-butyl 3-methyl 4-(tert-butyldimethylsilyloxy)piperidine-1,3 dicarboxylate from step A in THF (100 mL) was cooled at 0° C. and then LiBH4 (1.10 g, 50 mmol) was added in. After stirring for 2 hours as the solution was warmed to room temperature, the pH value was adjusted to 4 with 1M citric acid. Aft... | CC(C)(C)OC(=O)N1CCC(O[Si](C)(C)C(C)(C)C)C(CO)C1 | null | 100 | null |
1,770,040 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | Cl[C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=O.[S:13]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH2:21])=[O:20])=[CH:14]1>>[C:9]1([C@H:18]2[C@H:18]([C:15]3[CH:16]=[CH:17][S:13][CH:14]=3)[C:19](=[O:20])[NH:21][C:19]2=[O:20])[C:3]2=[C:4]3[C:5](=[CH:6][CH:7]=[CH:2]2)[CH2:16][CH2:15][CH2:14][N:12]3[CH:10]... | NC(=O)Cc1ccsc1 | NC(=O)Cc1ccc(F)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (±)-Trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1yl)-4-(thiophen-3-yl)pyrrolidine-2,5-dione was prepared according to Example 40 replacing 2-chloro-4-fluorophenylacetamide with thiophen-3-ylacetamide. Yield 50.3 mg, 15.0%. 1H NMR (DMSO-d6) 400 MHz δ: 11.50 (s, 1H), 7.52 (m, 1H), 7.49 (m, 1H), 7.35 (s, 1H), 7.21 (... | O=C1NC(=O)[C@@H](c2cn3c4c(cccc24)CCC3)[C@@H]1c1ccsc1 | null | null | null |
818,915 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:36][C:37]1[C:69]([C:70]([F:73])([F:72])[F:71])=[CH:68][CH:67]=[CH:66][C:38]=1[CH2:39][N:40]([CH2:52][CH:53]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:5... | CC(C)(C)OC(=O)NCc1cccc(O)c1 | Nc1cccc(OCCCN(Cc2cccc(C(F)(F)F)c2Cl)CC(c2ccccc2)c2ccccc2)c1 | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | (3-Hydroxy-benzyl)-carbamic acid tert butyl ester was dissolved in THF, triphenylphosphine (0.44 g, 2.2 mmole), 3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethylamino]-propoxy}-phenylamine (1.0 g, 2.3 mmole) and DIAD (0.43 ml, 2.2 mmole) were added subsequently. The mixture was stirred overnight at room tempe... | CC(C)(C)OC(=O)NCc1cccc(OCCCN(Cc2cccc(C(F)(F)F)c2Cl)CC(c2ccccc2)c2ccccc2)c1 | null | 48 | null |
432,045 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.Cl.[CH2:9]([N:11]([CH2:14][CH2:15]Cl)[CH2:12][CH3:13])[CH3:10].[OH-].[K+]>CO>[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:10][CH2:9][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[N:5][N:6]=1 | Nc1nnc(S)s1 | CCN(CC)CCCl | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 2-Amino-5-mercapto-1,3,4-thiadiazole (13.3 g), diethylaminoethylchloridehydrochloride (17.2 g), and potassium hydroxide (11.2 g) were stirred in methanol (200 ml) overnight at room temperature. The reaction mixture was concentrated under a vacuum. The residue, with water added thereto, was extracted with ethyl acetate.... | CCN(CC)CCSc1nnc(N)s1 | null | 81.9 | null |
1,608,182 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH:8]([N:12]2[CH:16]=[C:15]([C:17]3[C:18]4[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:19]=4[N:20]=[CH:21][N:22]=3)[CH:14]=[N:13]2)[CH2:9][CH:10]=O)[CH:5]=[CH:6][CH:7]=1.CN(C)C(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:60](Br)([F:62])[F:61]>... | FC(F)(Br)Br | C[Si](C)(C)CCOCn1ccc2c(-c3cnn(C(CC=O)c4cccc(Br)c4)c3)ncnc21 | null | [Zn] | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 3-(3-bromophenyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanal (0.05 g, 0.00009 mol) in N,N-dimethylacetamide (2 mL, 0.02 mol) was added triphenylphosphine (0.1 g, 0.0006 mol), dibromodifluoromethane (50 uL, 0.0006 mol) and 0.76 M zinc in THF (0.7 m... | C[Si](C)(C)CCOCn1ccc2c(-c3cnn(C(CC=C(F)F)c4cccc(Br)c4)c3)ncnc21 | null | 39.6 | null |
1,212,288 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(N(CC)CC)C>C1COCC1>[CH2:19]([O:18][C:16](=[O:17])[NH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12]... | CC(C)(C)OC(=O)N1CC[C@H](CN)C1 | O=C(Cl)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 4 | A solution of (R)-tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate (1.0 g, 5.0 mmol) and 50 mL THF was cooled in an ice bath. To this mixture was added benzyl chloroformate (0.77 mL, 5.5 mmol), followed by triethylamine (1.39 mL, 10 mmol). After removing the ice bath, the reaction was stirred for 4 h. The mixture wa... | CC(C)(C)OC(=O)N1CC[C@H](CNC(=O)OCc2ccccc2)C1 | null | 77.2 | null |
428,961 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10]1([CH3:21])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]=O)[C:12]=2[O:11]1>C(O)(=O)C>[CH3:9][C:10]1([CH3:21])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([CH2:19][NH:1][C:2]3[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=3)[C:12]=2[O:11]1 | CC1(C)Cc2cccc(C=O)c2O1 | Nc1cccnc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 5 g of 3-amino-2-chloropyridine was dissolved in 80 ml of acetic acid, and 7.1 g of 2,2-dimethyl-7-formyl-2,3-dihydrobenzofuran was added. Then, the mixture was stirred at room temperature for about 30 minutes, and 16.5 g of triacetoxy sodium borohydride was added gradually under ice-cooling. After stirring the obtaine... | CC1(C)Cc2cccc(CNc3cccnc3Cl)c2O1 | null | 108.6 | null |
1,059,901 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])=[C:18]([O:28][CH3:29])[CH:17]=3)=[O:14])[NH:11][CH:12]=2)=[CH:4][CH:3]=1.Br[CH2:31][CH2:32]Br>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:13](=[O:14])[N:15]([C:16]4[C... | BrCCBr | COc1cc(NC(=O)c2cc(-c3ccc(Cl)cc3)c[nH]2)ccc1OCC(C)(C)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure described in Example 1 step D, the product of step B (11 mg) was alkylated with 1,2-dibromoethane to yield 1.8 mg of the title compound. MS (ESI) 441 (M+H)+. | COc1cc(N2CCn3cc(-c4ccc(Cl)cc4)cc3C2=O)ccc1OCC(C)(C)O | null | null | null |
252,986 | ord_dataset-49bd993346b64eeeb2a8fe2643164a0a | null | 1992-01-01T00:08:00 | true | Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:3].C[Si](C)(C)[N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20]>C1(C)C=CC=CC=1>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])=[O:3])=[CH:6][CH:7]=1 | C[Si](C)(C)N1CCCC1=O | COc1ccc(OC(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of 4-methoxyphenyl chloroformate (3.73 g, 20.2 mmol) in anhydrous toluene (10 ml) was added a solution of 1-trimethylsilyl-2-pyrrolidinone (3.46 g, 22.0 mmol) in anhydrous toluene (10 ml). The mixture was stirred at room temperature for 30 min. The reaction mixture was evaporated under reduced pressure to... | COc1ccc(OC(=O)N2CCCC2=O)cc1 | null | 72.6 | null |
569,382 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [F:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:8]=[C:9]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[F:30][C:31]([F:36])([F:35])[CH:32]1[O:34][CH2:33]1>C(#N)C.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.F... | FC(F)(F)C1CO1 | Fc1ccc(Oc2cccc(NCc3cccc(OC(F)(F)C(F)F)c3)c2)cc1 | null | O=S(=O)([O-])C(F)(F)F | [Yb+3] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 40 | null | The N-[3-(4-fluorophenoxy)phenyl][[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amine (612 mg, 1.5 mmol) product from EX-634C and 1,1,1-trifluoro-2,3-epoxypropane (268 mg, 2.4 mmol) were dissolved in 1.0 mL of acetonitrile. Ytterbium (III) trifluoromethanesulfonate (43 mg, 0.07 mmol) was added, and the stirred solution w... | OC(CN(Cc1cccc(OC(F)(F)C(F)F)c1)c1cccc(Oc2ccc(F)cc2)c1)C(F)(F)F | null | 80.9 | null |
1,078,143 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15](C=O)=[C:11]2[O:12][C:13]=1[CH3:14].C1C=C(Cl)C=C(C(OO)=[O:29])C=1.C([O-])([O-])=O.[K+].[K+].CO>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([OH:29])=[C:11]2[O:12][C:13]... | O=C(OO)c1cccc(Cl)c1 | Cc1nn2c(-c3ccc(Cl)cc3Cl)c(C)oc2c1C=O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 0 | null | 3-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole-7-carbaldehyde (750 mg, 2.426 mmol) and m-CPBA (897 mg, 3.64 mmol) are stirred in DCM (10.5 ml) at RT for 3 hours, whereupon the reaction mixture is diluted with DCM (120 ml). The organic phase is washed with sat. NaHCO3 (70 ml) and the phases separated via a ... | Cc1nn2c(-c3ccc(Cl)cc3Cl)c(C)oc2c1O | null | null | null |
1,071,991 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19])=[CH:4][CH:3]=1 | Sc1ccc(Cl)cc1 | COC(CBr)OC | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 24 | To a solution of 4-chlorobenzenethiol (5.78 g; 40 mmol) in anhydrous acetone (50 mL) was added potassium carbonate (5.52 g, 40 mmol) and dropwise at room temperature 2-bromo-1,1-dimethoxy-ethane (4.7 mL, 40 mmol). After 24 h of stirring, the precipitate was filtered, the filtrate concentrated, the residue diluted with ... | COC(CSc1ccc(Cl)cc1)OC | null | 98 | null |
77,147 | ord_dataset-8c94910e81cc4281bd57a58ce657576f | null | 1981-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[C:4]([N:6]([CH:15]([CH3:19])[C:16](O)=[O:17])[C:7]1[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[CH:9][CH:8]=1)=[O:5].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:29][CH:28]=1>>[Cl:1][C:2]1[CH:23]=[C:22]([... | COc1ccc(N(C(=O)c2ccc(Cl)cc2Cl)C(C)C(=O)O)cc1 | COC(=O)CCCNc1ccc(OC)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Analogously to Example 1, by using equivalent quantities, reacting N-(2,4-dichlorobenzoyl)-2-(p-anisidino)propionic acid and methyl 4-(p-anisidino)butyrate and suitable processing produces methyl N-[N-(2,4-dichlorobenzoyl)-2-(p-anisidino)propionyl]-4-(p-anisidino)butyrate (oil), saponification of which and processing o... | COC(=O)CCCN(C(=O)C(C)N(C(=O)c1ccc(Cl)cc1Cl)c1ccc(OC)cc1)c1ccc(OC)cc1 | null | null | null |
748,990 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[O:10])=[CH:4][CH:3]=1.Cl[CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15... | O=C(NCC1CNCCO1)Nc1ccc(Cl)cc1 | ClCc1cccc2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 2 | To a stirred solution of Intermediate 9 (0.01 g) in N,N-dimethylformamide (1 ml) was added 1-(chloromethyl)naphthalene (6.1 μl). The mixture was stirred at 22° C. for 24 h before tris-(2-aminoethyl)amine polystyrene (Argonaut Technologies, 0.01 g @ 4.46 mmol/g) and polystyrene methyl isocyanate (Argonaut Technologies, ... | O=C(NCC1CN(Cc2cccc3ccccc23)CCO1)Nc1ccc(Cl)cc1 | null | null | null |
584,747 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].O[CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[Br:1]... | CC(C)(C)OC(=O)NCCO | CCOC(=O)C(Cc1ccc(O)c(Br)c1)Oc1ccccc1 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | In a similar manner to that described in Example 122, a reaction was carried out using ethyl 3-(3-bromo-4-hydroxyphenyl)-2-phenoxypropionate (374 mg), which is the product of Reference example 52(a), t-butyl 2-hydroxyethylcarbamate (403 mg), triphenylphosphine (672 mg) and a solution of diethylazodicarboxylate in tolue... | CCOC(=O)C(Cc1ccc(OCCNC(=O)OC(C)(C)C)c(Br)c1)Oc1ccccc1 | null | 89.5 | null |
946,202 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | Cl[C:2]1([Cl:8])[CH2:7][O:6][CH2:5][CH2:4][O:3]1.[N+:9]([C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1)([O-:11])=[O:10]>>[Cl:8][CH2:2][CH2:7][O:6][CH2:5][C:4]([NH:16][C:15]1[CH:17]=[CH:18][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=1)=[O:3] | ClC1(Cl)COCCO1 | Nc1ccc([N+](=O)[O-])cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 80 | 1 | 1.53 g of a mixture of 2-chlorodioxene and 2,2-dichlorodioxane (molar ratio 1:1) are added to 1.00 g (7.24 mmol) of 4-nitroaniline, and the mixture is heated to 80° C. with stirring. A solid brown mass forms within one hour and becomes liquid again and crystallises within the following 12 hours. The crude product is re... | O=C(COCCCl)Nc1ccc([N+](=O)[O-])cc1 | null | null | null |
1,285,281 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:15][C:16]2[C:24]3[C:23]([C:25]([O:27]C)=[O:26])=[CH:22][CH:21]=[N:20][C:19]=3[N:18](C(OC(C)(C)C)=O)[CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:15][C:16]2[C:2... | COC(=O)c1ccnc2c1c(CNCC1CCN(C(=O)OC(C)(C)C)C1)cn2C(=O)OC(C)(C)C | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 1-tert-butyl 4-methyl 3-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (70 mg, 0.143 mmol) in dioxane (2 mL) was added 1N LiOH (0.358 mL, 0.358 mmol) at 0° C. and stirred for 4 h at rt. The reaction mixture was extracted with ether and the aque... | CC(C)(C)OC(=O)N1CCC(CNCc2c[nH]c3nccc(C(=O)O)c23)C1 | null | null | null |
571,627 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [CH3:1][O:2][C:3](=[O:15])[N:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13]Br)[O:5][CH3:6].C[N+]1([O-])CC[O:20]CC1>C(#N)C>[CH3:1][O:2][C:3](=[O:15])[N:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=[O:20])[O:5][CH3:6] | C[N+]1([O-])CCOCC1 | COC(=O)N(OC)c1ccccc1CBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | 16 | A solution of 27.4 g of (2-bromomethyl-phenyl)-N-methoxycarbamic acid methyl ester in 50 ml of acetonitrile is added dropwise at room temperature to 40 g of N-methyl-morpholine-N-oxide in 150 ml of acetonitrile. After stirring for 16 hours, the mixture is concentrated and the residue partitioned between ethyl acetate a... | COC(=O)N(OC)c1ccccc1C=O | null | null | null |
603,431 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([C:30](O)=[O:31])[C:25]=1[CH3:33])(=[O:12])=[O:11].CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[NH2:50][CH2:51][CH2:52][N:53]1[CH2:58][CH2:57]... | Cc1[nH]c(/C=C2\C(=O)Nc3ccc(S(=O)(=O)Cc4c(Cl)cccc4Cl)cc32)c(C)c1C(=O)O | NCCN1CCC(O)CC1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 0.75 | A mixture of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (100 mg, 0.19 mmol), DIPEA (115 mg, 5 eq.) and 1-(2-amino-ethyl)-piperidin-4-ol TFA salt (88 mg, 1.2 eq.) in 2 mL) was stirred at rt for 45 mins. To the mixture was added HATU (83... | Cc1[nH]c(/C=C2\C(=O)Nc3ccc(S(=O)(=O)Cc4c(Cl)cccc4Cl)cc32)c(C)c1C(=O)NCCN1CCC(O)CC1 | null | null | null |
117,424 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.CS(C)=O.[OH-].[K+].[CH2:24](OS(OCC)(=O)=O)[CH3:25]>C1(C)C=CC=CC=1>[CH2:24]([N:9]([CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[C... | COc1ccc(NCCc2ccccn2)cc1 | CCOS(=O)(=O)OCC | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CS(C)=O | null | null | null | null | null | null | null | null | null | 40 | null | With stirring 10.6 g (0.044 mole) of N-[2-(2-pyridyl)ethyl]-4-methoxy-aniline, prepared in a manner similar to that described in Example 1, part A, was added to 25.0 ml of dimethylsulfoxide. After the solution was complete, 4.9 g of ground potassium hydroxide was added slowly to the solution maintaining a temperature u... | CCN(CCc1ccccn1)c1ccc(OC)cc1 | null | 48.8 | null |
1,008,604 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH:1]1([CH2:4][N:5]([CH2:18][CH2:19][OH:20])[C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=2)[CH2:3][CH2:2]1.[F:21][C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1>>[CH:1]1([CH2:4][N:5]([CH2:18][CH2:19][O:20][C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)[C:6]2[CH:13]=[CH:12... | N#Cc1ccc(N(CCO)CC2CC2)cc1C(F)(F)F | Oc1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesized as described in Example 1C from 4-[(cyclopropylmethyl)(2-hydroxyethyl)amino]-2-(trifluoromethyl)benzonitrile and 4-fluorophenol: MS (APCI) m/z 379 (M+1). | N#Cc1ccc(N(CCOc2ccc(F)cc2)CC2CC2)cc1C(F)(F)F | null | null | null |
806,124 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [C-]#N.[Na+].C1(C)C=CC=CC=1.C[NH:12][CH2:13][CH2:14]NC.BrC1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1>N>[CH3:25][C:20]1[CH:19]=[C:14]([CH:23]=[C:22]([CH3:24])[CH:21]=1)[C:13]#[N:12] | CNCCNC | Cc1cc(C)cc(Br)c1 | null | N | [C-]#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 110 | 24 | An oven dried 100 mL three necked round bottom flask was charged, under positive pressure of argon, with NaCN (2.04 g, 41.6 mmol) CuI (660 mg, 3.47 mmol, 10 mol %), KI (1.14 g, 6.87 mmol, 20 mol %), and anhydrous toluene (25 mL). N,N′-Dimethylethylenediamine (3.7 mL, 35 mmol) and 5-bromo-m-xylene (4.7 mL, 35 mmol) were... | Cc1cc(C)cc(C#N)c1 | null | 88.9 | null |
1,434,416 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]CCCC.[I:34]I>C(OCC)C.C1COCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:12][C:13]=1[I:34]... | II | CC(C)(C)OC(=O)Nc1ccc(-c2ccccc2)nc1 | null | CN(C)CCN(C)C | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | -10 | 0.25 | A solution of (6-phenylpyridin-3-yl)carbamic acid tert-butyl ester (5.54 g, 20.5 mmol) and TMEDA (6.49 mL, 43.0 mmol) in 100 mL of anhydrous diethyl ether was treated with n-BuLi at −78° C. After 15 minutes at −78° C., the mixture was warmed to −10° C. and stirred for an additional 3 hours. The reaction mixture was the... | CC(C)(C)OC(=O)Nc1cnc(-c2ccccc2)cc1I | null | 11 | null |
1,605,197 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[CH:12]=[C:13](/[C:16](=O)[CH3:17])\[C:14]#[N:15])[CH:10]=2)[NH:5][N:4]=1)[CH3:2].[CH3:19][C:20]1[CH:24]=[C:23]([NH2:25])[O:22][N:21]=1>>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]3[C:13]([C:14]#[N:15])=[C:16]([CH3:17])[NH:25][C:23]4[O:22][N:21]=[C:20]([CH3:19]... | Cc1cc(N)on1 | CCc1n[nH]c2ccc(/C=C(\C#N)C(C)=O)cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 mg (0.42 mmol) (2E)-2-[(3-ethyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 18A) were treated with 3-methyl-1,2-oxazol-5-amine following the procedure described in Example 2. The crude material was purified by preparative RP-HPLC (methanol/water+0.1% TFA gradient) to yield 51 mg (38% of th.) of the rac... | CCc1n[nH]c2ccc(C3C(C#N)=C(C)Nc4onc(C)c43)cc12 | null | null | null |
1,134,046 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | Br[C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:10][CH:9]=1)=[O:6].[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1B(O)O>>[N:21]1([CH2:20][CH2:19][O:18][C:11]2[C:... | Cc1ccc(C)c(B(O)O)c1 | O=C(Nc1ccc(OCCN2CCOCC2)c2ccccc12)c1cccc(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Compound is prepared from 3-bromo-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-benzamide and 2,5-dimethylphenyl boronic acid according to conditions described in general procedure K. 1H NMR 300 MHz (CDCl3) δ 8.3(d, 1H), 7.4-8.05(m, 9H), 7.2(d, 1H), 7.1(d, 2H), 6.8(d, 1H), 4.3(t, 2H), 3.75(m, 4H), 3.0(t, 2H), 2.7(m, ... | Cc1ccc(C)c(-c2cccc(C(=O)Nc3ccc(OCCN4CCOCC4)c4ccccc34)c2)c1 | null | null | null |
892,388 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[O:25])[CH3:24]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:16][C:17]1[... | COc1cc2nccc(Cl)c2cc1OC | CC(=O)c1ccccc1O | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1Cl | null | null | null | null | null | null | null | null | null | null | 160 | 11 | 4-Chloro-6,7-dimethoxyquinoline (58.1 mg), 2′-hydroxyacetophenone (361 mg), and 4-dimethylaminopyridine (317 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 11 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillati... | COc1cc2nccc(Oc3ccccc3C(C)=O)c2cc1OC | null | 42.9 | null |
1,736,616 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH2:1]([O:8][C@H:9]([C@@H:29]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C@H:30]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:31](=O)[CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][C:20]2[CH:25]=[CH:... | CCOc1ccc(Cc2cc(C(=O)[C@H](OCc3ccccc3)[C@@H](OCc3ccccc3)[C@H](OCc3ccccc3)C(=O)COCc3ccccc3)ccc2Cl)cc1 | [BH3-]C#N | null | N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | A solution of compound from step C (400 mg, 0.5 mmol), 7N ammonia in MeOH (1.0 mL) and freshly activated 4 Å molecular sieves (250 mg) in dichloromethane (20 mL) were refluxed overnight. The reaction mixture was cooled to room temperature, then sodium cyanoborohydride (160 mg, 2.55 mmol) was added and refluxed for addi... | CCOc1ccc(Cc2cc(C3NC(COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H](OCc4ccccc4)[C@H]3OCc3ccccc3)ccc2Cl)cc1 | null | 35.4 | null |
490,627 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | O[C:2]1([OH:11])[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[CH:3]1[OH:10].[CH3:12][CH2:13][O:14]CC.C(#N)C.Cl>[Cl-].[Zn+2].[Cl-].O>[OH:11][C:2]1[C:3]([OH:10])=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[C:7]=1[C:13]([CH3:12])=[O:14] | CCOCC | OC1=CC(O)(O)C(O)C(O)=C1 | null | Cl | [Cl-] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | 0 | 13 | Under a stream of argon, 2.00 g (14.08 mmol) of 1,2,3,5-tetrahydroxyphenol (3) and 20 ml of ether were placed to form a suspension and 1.00 g (24.3 mmol, 1.73 equivalents) of acetonitrile was added to the suspension. While the resultant mixture was cooled with ice water, 0.70 g (5.14 mmol, 0.36 equivalent) of zinc chlo... | CC(=O)c1c(O)cc(O)c(O)c1O | null | 31.8 | null |
116,704 | ord_dataset-19041548671f410397ce7f00536a9be3 | null | 1984-01-01T00:04:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C[O-].[Na+].Cl[CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1.Cl>CO.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9])[CH2:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1 | ClCc1c[nH]cn1 | Cc1cccc(C)c1O | null | C[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | null | To a solution of 12.2 g of 2,6-dimethylphenol in methanol are added 20 ml of 30% sodium methoxide solution, and the resultant mixture is warmed to 50° C. The mixture is maintained at that temperature while 5.8 g of 4-chloromethylimidazole in methanol are added, with stirring. After the addition is complete, the reactio... | Cc1cc(Cc2c[nH]cn2)cc(C)c1O | null | 54 | null |
1,481,644 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([B:14]3[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1.[CH3:23][N:24]([CH3:35])[CH2:25][CH2:26][O:27][C:28]1[CH:34]=CC(N)=C[CH:29]=1>>[CH3:23][N:24]([CH3:35])[CH2:25][CH2:26][O:27][C:28]1[CH:34]=[CH:3][C:1]([... | CC1(C)OB(c2ccc(NC(=O)NC3CC3)cc2)OC1(C)C | CN(C)CCOc1ccc(N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A procedure analogous to that used for the preparation of 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea was used, using 4-(2-(dimethylamino)ethoxy)aniline as the amine component. | CN(C)CCOc1ccc(NC(=O)Nc2ccc(B3OC(C)(C)C(C)(C)O3)cc2)cc1 | null | null | null |
1,141,646 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[O:3])[NH2:2].Br[CH2:18][C:19](=O)[C:20]([F:23])([F:22])[F:21]>O1CCOCC1>[F:21][C:20]([F:23])([F:22])[C:19]1[N:2]=[C:1]([NH:4][C:5]2[CH:6]=[CH:7][C:8]([C@@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2... | O=C(CBr)C(F)(F)F | COC(=O)[C@H](C)c1ccc(NC(N)=O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of methyl (2R)-2-[4-(carbamoylamino)phenyl]propanoate (2.7 g, 9.95 mmol) in dioxane (50 ml) was treated at room temperature with 3-bromo-1,1,1-trifluoro-propan-2-one (1.03 ml, 10 mmol) and the resulting mixture was refluxed for 2 h. After cooling at room temperature, the solvent was evaporated under vacuum, ... | COC(=O)[C@H](C)c1ccc(Nc2nc(C(F)(F)F)co2)cc1 | null | 80 | null |
294,656 | ord_dataset-bb4579c57ddc48c6a01fad97dacb6293 | null | 1994-01-01T00:08:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:11](=[O:21])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:22][N:23]=[C:24]=[O:25].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:22][NH:23][C:24](=[O:25])[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][C:11](=[O:21])[N:1... | O=C1CCC(c2ccc(O)cc2)N1CCN1CCOCC1 | CN=C=O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 5-(4-hydroxyphenyl)-1-[2-(4-morpholinyl)ethyl]pyrrolidin-2-one (0.99 g) in dry tetrahydrofuran (50 ml) was added methyl isocyanate (0.22 ml) at ambient temperature, with stirring, over ten mins. Milled potassium carbonate (0.565 g) was added, the reaction mixture was stirred for 2 days and filtered thr... | CNC(=O)Oc1ccc(C2CCC(=O)N2CCN2CCOCC2)cc1 | null | 52.3 | null |
511,171 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:23]=2[N:24]=[C:25]([Cl:27])[N:26]=1)[C@@H:15]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](Cl)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:37]1[CH:44]=[CH:43][C:40]([O:41][CH3:42])=[CH:39][CH:3... | O=C(Nc1nc(Cl)nc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1)c1ccccc1 | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | Compound 123 was prepared from compound 122 as per the procedure of example 107 using compound 122 (2.5 g, 6.43 mmol), DMTCl (2.37 g, 7 mmol), dry TEA (0.71 g, 7 mmol) and dry pyridine (100 ml). The crude product was purified by flash chromatography using methylene chloride→ethyl acetate containing 18 TEA as the eluent... | COc1ccc(C(OC[C@H]2O[C@@H](n3cnc4c(NC(=O)c5ccccc5)nc(Cl)nc43)C[C@@H]2O)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | null |
1,687,560 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[Cl:18][C:19]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[C:22]([Cl:28])[C:20]=1[NH2:21].[H-].[Na+]>O=S(Cl)Cl.C1COCC1>[Cl:18][C:19]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[C:22]([Cl:28])[C:20]=1[NH:21][C:4](=[O:... | COc1ccc(Cl)c(N)c1Cl | O=C(O)c1cc(-c2cccc(F)c2)ccc1F | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of 2-fluoro-5-(3-fluorophenyl)benzoic acid (intermediate III(a)) (1.6 g, 7 mmol, 3.0 eq) in SOCl2 (20 mL) was heated at reflux for 3 h. The excess thionyl chloride was removed in vacuo and the residue obtained dissolved in THF (10 mL) and added dropwise to a solution of 2,6-dichloro-3-methoxy-aniline (450 mg... | COc1ccc(Cl)c(NC(=O)c2cc(-c3cccc(F)c3)ccc2F)c1Cl | null | 21.3 | null |
1,551,860 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH:24][CH3:25])=[CH:19][CH:18]=1.BrB(Br)Br>>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([CH2:... | CNCc1ccc(-c2c(OC)ccc3[nH]c(=O)c4sccc4c23)cc1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following General Procedure F, 8-methoxy-9-{4-[(methylamino)methyl]phenyl}thieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.29 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 1.7 mL, 1.7 mmol) to afford the desired product (28 mg, 30%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.65 (d, J=8.1 Hz, 2H), 7.5... | CNCc1ccc(-c2c(O)ccc3[nH]c(=O)c4sccc4c23)cc1 | null | 28.7 | null |
553,829 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:39][CH3:40])=[C:6]([CH2:8][C:9]2[N:13]3[N:14]=[C:15](Cl)[CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[CH2:19][N:20]([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[C:24]=2[Cl:33])=[O:22])[CH:7]=1.[CH3:41][NH2:42].C1COCC1>CS(C... | CN | COc1ccc(Br)cc1Cc1c(CN(CCC(C)C)C(=O)c2ccc(OC)c(OC)c2Cl)nc2ccc(Cl)nn12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 150 | null | A solution of 130 mg (0.2 mmol) N-({3-[(5-bromo-2-methoxyphenyl)methyl]-6-chloro(imidazolo[1,2-b]pyridazin-2-yl)}methyl)(2-chloro-3,4-dimethoxyphenyl)-N-(3-methylbutyl)carboxamide in DMSO (3 mL) is treated with 2M methyl amine in THF 1.5 mL (3.0 mmol). The reaction mixture is heated to 150° C. in a sealed tube for 18 h... | CNc1ccc2nc(CN(CCC(C)C)C(=O)c3ccc(OC)c(OC)c3Cl)c(Cc3cc(Br)ccc3OC)n2n1 | null | 24 | null |
1,640,944 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | O.[CH3:2][N:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5]([CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4]1.C(=O)([O-])O.[Na+].[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=[CH:32][C:33](ON1C(=O)CCC1=O)=[O:34])#[N:24]>O1CCOCC1>[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=[CH:... | N#Cc1ccccc1C=CC(=O)ON1C(=O)CCC1=O | Cn1cc(C[C@H](N)C(=O)O)c2ccccc21 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To water (60 mL)-dioxane (60 mL) suspension of 1-methyl-L-tryptophan (2.1 g) was added sodium hydrogencarbonate (0.8 g) at 0° C., and the mixture was stirred for 30 minutes at room temperature. Dioxane (80 mL) solution of 2,5-dioxopyrrolidin-1-yl 3-(2-cyanophenyl)acrylate (2.5 g, 9.2 mmol) was added dropwise to the rea... | Cn1cc(C[C@H](NC(=O)C=Cc2ccccc2C#N)C(=O)O)c2ccccc21 | null | 27.9 | null |
1,668,037 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[OH:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[O:21][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:... | Cc1cccc(C)c1O | COc1ccc(C=O)cc1CCl | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 3-(chloromethyl)-4-methoxybenzaldehyde (300 mg, 1.625 mmol, 1.0 equivalent) and 2,6-dimethylphenol (218 mg, 1.787 mmol, 1.1 equivalent) in 10 ml acetonitrile was added potassium carbonate (1.1 g, 8.12 mmol, 5.0 equivalents). The mixture was heated to 150 C in a microwave for 30 min. Upon completion, th... | COc1ccc(C=O)cc1COc1c(C)cccc1C | null | 91.1 | null |
522,753 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [NH2:1][C:2]1[N:3]=[CH:4][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[C:6]=1[C:7]([NH2:9])=[O:8].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]2[N:3]=[CH:4][N:5]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13... | O=C(Cl)c1ccc(F)cc1 | Cc1ccc(Cn2cnc(N)c2C(N)=O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | An amidation reaction and post-treatment were carried out following the conditions of Example 1, using 2.30 g (9.99 mmol) of 4-amino-1-(4-methylbenzyl)-5-imidazolecarboxamide prepared in the same manner as in Example 87 and 4-fluorobenzoyl chloride instead of benzoyl chloride to obtain 2.26 g of 4-(4-fluorobenzoylamino... | Cc1ccc(Cn2cnc(NC(=O)c3ccc(F)cc3)c2C(N)=O)cc1 | null | 64 | null |
1,173,238 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([OH:25])=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.[F:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30... | O=C(O)COc1ccc(-c2ccc(F)cc2)nc1 | Nc1ccccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared analogously as described in Example 30(d) from 95 mg (0.26 mmol) of [6-(4-fluoro-phenyl)-pyridin-3-yloxy]-acetic acid trifluoroacetic acid salt and 43.8 mg (0.39 mmol) of 2-fluoroaniline. Yield: 9 mg. | O=C(COc1ccc(-c2ccc(F)cc2)nc1)Nc1ccccc1F | null | null | null |
177,842 | ord_dataset-3ef78abb9a384506b240a419b70e6ceb | null | 1988-01-01T00:09:00 | true | [F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]([CH2:18][C:19]([OH:21])=O)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.[C:24](N1C=CN=C1)([N:26]1C=CN=[CH:27]1)=O.CNC>O1CCCC1>[CH3:24][N:26]([CH3:27])[C:19](=[O:21])[CH2:18][N:17]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[N:10]=[C... | O=C(O)Cn1c(-c2ccc(C(F)(F)F)cc2)nc2cccnc21 | O=C(n1ccnc1)n1ccnc1 | null | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A suspension of 2-(4-trifluoromethylphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (10.0 g, 0.031 mole), 1,1'-carbonyldiimidazole (6.0 g, 0.037 mole), and dry tetrahydrofuran (200 ml) was stirred at room temperature for 2 hr. with a stream of nitrogen bubbling through it. The suspension was heated at 50° C. under nitr... | CN(C)C(=O)Cn1c(-c2ccc(C(F)(F)F)cc2)nc2cccnc21 | null | 32.9 | null |
20,258 | ord_dataset-2a1960001e7d4e89987253631df1362a | null | 1977-01-01T00:02:00 | true | [F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][NH:11][C:10]2=[O:19])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[F:21][C:2]([F:20])([F:1])[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]([CH3:24])[C:10]2=[O:19])[CH:6]=[C... | CI | O=C1NCc2cccnc2N1c1cccc(C(F)(F)F)c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 100 | null | To a solution of 0.7 g of 1-(m-trifluoromethylphenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 10 ml of dimethylformamide was added 0.13 g of sodium hydride. To this was added a mixture of 5.1 g of methyl iodide and 5 ml of dimethylformamide, dropwise under cooling, and immediately the resulting mixture was ... | CN1Cc2cccnc2N(c2cccc(C(F)(F)F)c2)C1=O | null | 81.8 | null |
939,122 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [F:1][C:2]([F:22])([F:21])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([CH2:19][OH:20])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:4]>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]([F:21])([F:22])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][C:12]([CH:19]=[O:20])=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[CH2:9][... | O=C(N[C@@H]1CCCc2cc(CO)c([N+](=O)[O-])cc21)C(F)(F)F | null | null | O=[Mn]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 3 | To a solution of (R)-2,2,2-trifluoro-N-(6-(hydroxymethyl)-7-nitro-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (350 mg, 1.1 mmol) in 100 mL of DCM was added portion wise MnO2 (957 mg, 11 mmol). After stirring at RT for 3 h, the reaction mixture was filtered though silica gel with the help of hexane/EtOAc=1:1 to give ((R... | O=Cc1cc2c(cc1[N+](=O)[O-])[C@H](NC(=O)C(F)(F)F)CCC2 | null | null | null |
215,087 | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | null | 1990-01-01T00:09:00 | true | [OH:1][CH:2]1[CH2:6][CH2:5][C:4]2([CH2:11][C:10](=[O:12])[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][Br:17])[C:8](=[O:18])[CH2:7]2)[CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:6][CH2:5][C:4]2([CH2:7][C:8](=[O:18])[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][Br:17])[C:10](=[O:12])[CH2:11]2)[CH2:3]1 | O=C1CC2(CCC(O)C2)CC(=O)N1CCCCBr | null | null | O=[Cr](=O)([O-])Cl | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | 2-Hydroxy-8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9dione-(15.92 g, 1.00 equiv) was dissolved in 100 mL of CH2Cl2 and added to a solution of PCC (120 g, 11 equiv) in 500 mL of CH2Cl2 and stirred at room temperature for 2 h. The solution was filtered through a bed of celite and the salts were washed with CH2Cl2. The sol... | O=C1CCC2(C1)CC(=O)N(CCCCBr)C(=O)C2 | null | 98 | null |
1,583,395 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH:15]=[N:14][C:13]=1[C:21]#[N:22].Cl.O1CCOCC1>>[NH2:22][C:21]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][CH:18]([CH3:19])[CH3:20])[C:12]=2[C:3]2[CH:4]=[CH:5][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:2... | COC(=O)c1ccc(-c2c(C#N)ncn2CC(C)C)c(N)c1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | null | To 5-(2-amino-4-methoxycarbonylphenyl)-1-isobutyl-1H-imidazole-4-carbonitrile S12 (150 mg, 0.50 mmol, 1.0 equiv) was added 4 N HCl in dioxane (2.0 mL, 8.0 mmol, 16 equiv). The reaction was heated at reflux condition for 15 h then cooled to 25° C. The reaction was concentrated in vacuo and partitioned between 1:9 MeOH/E... | COC(=O)c1ccc2c(c1)nc(N)c1ncn(CC(C)C)c12 | null | 88 | null |
1,338,977 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [CH3:1][C:2]1([C:7]2[O:11][C:10]([CH2:12][N:13]3[N:17]=[C:16]([NH2:18])[CH:15]=[N:14]3)=[CH:9][CH:8]=2)[O:6]CCO1.[CH2:19]([C:23]1[O:24][C:25]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:26]([C:28](O)=[O:29])[N:27]=1)[CH2:20][CH2:21][CH3:22]>>[C:2]([C:7]1[O:11][C:10]([CH2:12][N:13]2[N:17]=[C:16]([NH:18][C:28]([C:... | CC1(c2ccc(Cn3ncc(N)n3)o2)OCCO1 | CCCCc1nc(C(=O)O)c(-c2ccccc2)o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following general procedure A followed by B, starting from 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-2H-[1,2,3]triazol-4-ylamine and 2-butyl-5-phenyl-oxazole-4-carboxylic acid. | CCCCc1nc(C(=O)Nc2cnn(Cc3ccc(C(C)=O)o3)n2)c(-c2ccccc2)o1 | null | null | null |
536,966 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[CH:4][C:3]=1[OH:20].[N+:21]([O-])([OH:23])=[O:22]>>[Cl:1][C:2]1[C:3]([OH:20])=[C:4]([N+:21]([O-:23])=[O:22])[C:5]([N:9]2[C:10](=[O:19])[C:11]3=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]3[C:13]2=[O:14])=[C:6... | O=C1c2ccccc2C(=O)N1c1cc(O)c(Cl)cc1F | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | null | 2-Chloro-4-fluoro-5-(phthalimido)phenol (5.0 g, 17.1 mmol) was slowly added with stirring to con. nitric acid (50 ml) at −10° C. Solution was then warned to ambient temperature. and allowed to stir for 0.5 hr. Addition to ice-water resulted in a light yellow precipitate which was separated by filtration to afford the t... | O=C1c2ccccc2C(=O)N1c1c(F)cc(Cl)c(O)c1[N+](=O)[O-] | null | null | null |
1,597,175 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](Br)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1([CH3:40])[C:30]2[C:25](=[CH:26][C:27](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:29]=2)[CH2:24][CH2:23]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH... | CC1(C)CCc2cc(B3OC(C)(C)C(C)(C)O3)ccc21 | CC(C)(C)OC(=O)N1CCN(c2cccc(Br)n2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The preparation is carried out analogously to FS 102 starting from 4-(6-bromopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (US 2005/176722) and 2-(1,1-dimethylindan-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. | CC(C)(C)OC(=O)N1CCN(c2cccc(-c3ccc4c(c3)CCC4(C)C)n2)CC1 | null | null | null |
338,562 | ord_dataset-4706e7a7f3cd421bb42b7f877cff8af9 | null | 1996-01-01T00:09:00 | true | [N:1]1([CH2:7][CH2:8][N:9]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=[O:20])[CH2:14][CH2:13][N:12]([CH2:22][C:23]([OH:25])=[O:24])[CH2:11][CH2:10]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[Na+].Br[CH2:29][C:30]([OH:32])=[O:31].Cl>O>[C:30]([CH2:29][N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][N:9]2[CH2:17][CH2:16][N:1... | O=C(O)CN1CCN(CCN2CCNCC2)CCN(CC(=O)O)CC1 | O=C(O)CBr | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 15 | A solution of 1-(2-piperazinoethyl)-4,7-bis-(carboxymethyl)-1,4,7-triazacyclononane (10.7 g, 0.03 mol) in 100 mL of deionized water is adjusted to pH 10 with 1N sodium hydroxide solution. Then bromoacetic acid (4.2 g, 0.03 mol) is added and the solution is heated at 50 C. for 15 hours, keeping the pH between 9 and 10 w... | O=C(O)CN1CCN(CCN2CCN(CC(=O)O)CCN(CC(=O)O)CC2)CC1 | null | null | null |
929,386 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [C:1]1([N:11]2[C:15]([S:16][CH2:17][C:18]([OH:20])=O)=[N:14][N:13]=[N:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH:24][C:18](=[O:20])[CH2:17][S:16][C:15]... | Nc1ccccc1Cl | O=C(O)CSc1nnnn1-c1cccc2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | 0 | 1 | 2-{{1-(1-Naphthalenyl)-1H-tetrazol-5-yl}thio}acetic acid (500 mg, 1.75 mmol) and 2-chloroaniline (202 μL, 1.92 mmol) were dissolved in dry pyridine (8 mL). This solution was cooled to 0° C. and POCl3 (0.179 mL) was added dropwise. The mixture was stirred at 0° C. for 1 h, quenched with a few drops of water, and concent... | O=C(CSc1nnnn1-c1cccc2ccccc12)Nc1ccccc1Cl | null | 92.8 | null |
904,282 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH3:1][N:2]1[C:14]2[CH:13]=[CH:12][C:11]([C:15]3[CH:24]=[CH:23][C:18]([O:19][CH2:20][C:21]#[N:22])=[CH:17][CH:16]=3)=[CH:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2.[N-:25]=[N+:26]=[N-:27].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][N:2]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[C:11]([C:... | [N-]=[N+]=[N-] | Cn1c2c(c3cc(-c4ccc(OCC#N)cc4)ccc31)CCCC2 | null | [Cl-] | [NH4+] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | The desired product was prepared using a procedure similar to step 6 of example 3. Thus, [4-(9-methyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetonitrile (0.149 g, 0.471 mmol) was reacted with NaN3 (0.153 g, 2.355 mmol) and NH4Cl (0.126 g, 2.355 mmol) in DMF (5 ml) to give the product (0.060 g, 0.167 mmol, 35%) ... | Cn1c2c(c3cc(-c4ccc(OCc5nnn[nH]5)cc4)ccc31)CCCC2 | null | null | null |
470,172 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1.C(O[C@@H:17]1[O:29][C@H:28]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])(=O)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>CC#N.CCOC(C)=O>[Cl:1][C:2]1[N:3]([C@@H:17]2[O:29][C@H:2... | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O | Clc1nc2cc(Cl)c(Cl)cc2[nH]1 | null | C[Si](C)(C)OS(=O)(=O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC#N | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a suspension of (5) (62.013 g, 280 mmol) in 1.4 L of dry MeCN under argon, was added 70 mL (280 mmol) of BSA. The reaction mixture was stirred at room temperature for 15 min to give a clear solution. To this solution were added 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose (89.096 g, 280 mmol) and then 60 mL (310 mmol) of... | CC(=O)OC[C@H]1O[C@@H](n2c(Cl)nc3cc(Cl)c(Cl)cc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | null |
437,485 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]12([CH2:22][NH2:23])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2>C1COCC1>[C:12]12([CH2:22][NH:23][C:4]([C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[C:1]([OH:6])=[O:11])=[O:5])[CH2:19][CH:18]3[CH2:17][CH:16]([CH... | NCC12CC3CC(CC(C3)C1)C2 | O=C1OC(=O)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | Phthalic anhydride (2.65 g, 17.9 mmol) was dissolved in dry THF (50 ml) and a solution of 1-adamantanemethylamine (2.96 g, 17.9 mmol) in THF (50 ml) was added. The mixture was stirred at room temperature for 16 h and the solution evaporated to dryness. The residue was triturated with hexane and the precipitate formed w... | O=C(O)c1ccccc1C(=O)NCC12CC3CC(CC(C3)C1)C2 | null | 96.6 | null |
454,206 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | [NH4+:1].[OH-].[CH:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CC(O)C>[CH:7]1[CH:8]=[CH:9][C:4](/[CH:3]=[N:1]/[CH:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)/[N:1]=[CH:3]/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:5][CH:6]=1 | [NH4+] | O=Cc1ccccc1 | null | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | 43 | To a 3 L 3-necked flask equipped with a mechanical stirrer and a thermometer was added I L of concentrated NH4OH (ca 30%) (14.8 moles). A solution of benzaldehyde (265 g, 2.50 mol) in 500 mL of 2-propanol was added in one portion. The mixture was stirred vigorously at ca 22° C. for 43 hr. The resulting slurry was filte... | C(=N/C(/N=C/c1ccccc1)c1ccccc1)\c1ccccc1 | null | 97.5 | null |
250,678 | ord_dataset-41ea179beba54bed8cd874a5ec3469f7 | null | 1992-01-01T00:07:00 | true | C[O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2>[OH-].[K+].CO.O.CO>[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:6]([CH2:5][CH2:4][C:3]([OH:16])=[O:2])[CH:7]=1 | COC(=O)CCc1cnc2ccccc2c1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | A solution of 3-quinolinepropanoic acid methyl ester (2.21 g, 10.3 mmol) in 10% KOH/MeOH (48.2 mL), H2O (20 mL) and methanol (134 mL) was stirred at room temperature for 3 h. Upon completion of reaction, the solution was concentrated and the aqueous residue was acidified to pH 5-6 with glacial HOAc. A crystalline solid... | O=C(O)CCc1cnc2ccccc2c1 | null | 88.7 | null |
1,197,064 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[IH:7].[CH3:8][N:9]1[CH2:13][CH2:12][N:11]=[C:10]1[NH:14][NH2:15]>N1C=CC=CC=1>[IH:7].[CH2:5]([O:4][C:2]([NH:15][NH:14][C:10]1[N:9]([CH3:8])[CH2:13][CH2:12][N:11]=1)=[O:3])[CH3:6] | CCOC(=O)Cl | CN1CCN=C1NN | null | I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | Ethyl chloroformate (0.95 ml) was added dropwise to a mixture of (1-methyl-4,5-dihydro-1H-imidazol-2-yl)-hydrazine hydroiodide (CAS 49541-82-4) (2 g) and pyridine (40 ml) while stirring, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off and the residue was purified by silica gel... | CCOC(=O)NNC1=NCCN1C | null | null | null |
278,071 | ord_dataset-ad17798fcea64e26ba91604fca520090 | null | 1993-01-01T00:10:00 | true | Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[NH:12]CC(O)COC1C2OC(C(=O)C)=CC=2C=CC=1>C(O)C>[NH2:12][CH:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1 | CC(=O)c1cc2cccc(OCC(O)CNC3CCc4ccccc4C3)c2o1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure described in Example 27, but starting from 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (23.2 g), obtained from 2-acetyl-7- hydroxybenzofuran and epichlorohydrin according to the teaching of Belgian Patent 783,440, and 2-aminotetralin (14.81 g) in ethanol (120 ml), N-(1,2,3,4-tetrahydronaphth-2-yl)-2... | NC1CCc2ccccc2C1 | null | null | null |
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