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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,144,988 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=O)[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4].[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([CH2:35]/[C:36](=[N:39]/[H])/[NH:37]O)[CH:31]=[CH:32][C:33]=1[OH:34])[CH3:26].[O-]CC.[Na+]>CCO>[CH2:1]([N:5]1[C:13]2[N:12]=[C:1... | CCCCn1c(=O)n(CCCC(=O)OCC)c(=O)c2[nH]c(Cl)nc21 | [H]/N=C(/Cc1ccc(O)c(OCC)c1)NO | null | CC[O-] | [Na+] | 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 | 140 | null | Ethyl 4-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoate (53 mg, 0.15 mmol) and (1Z)-2-[3-(ethyloxy)-4-hydroxyphenyl]-N-hydroxyethanimidamide (35 mg, 0.165 mmol; entry 11, Table 7) were mixed in EtOH (0.75 ml). Ethanolic sodium ethoxide (21% by wt., 0.083 ml, 0.22 mmol) was added and the mixture w... | CCCCn1c(=O)n(CCCc2nc(Cc3ccc(O)c(OCC)c3)no2)c(=O)c2[nH]c(Cl)nc21 | null | 39.2 | null |
1,359,847 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].O[C:11]1[CH:21]=[CH:20][CH:19]=[C:13]2[C:14]([NH:16][C:17](=[O:18])[C:12]=12)=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:7][O:6][C:4](=[O:5])[C:3]([CH3:9])([CH3:8])[CH2:2][O:1][N:16]1[C:17](=[O:18])[C:12]2[C:13](=[... | COC(=O)C(C)(C)CO | O=C1NC(=O)c2c(O)cccc21 | null | CC(C)OC(=O)N=NC(=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 | 0 | 12 | To methyl hydroxypivalate (1.31 g, 9.89 mmol) were added tetrahydrofuran (40 ml), hydroxyphthalimide (3.23 g, 19.78 mmol) and triphenylphosphine (6.48 g, 24.73 mmol). After this solution was cooled to 0° C., diisopropyl azodicarboxylate (4.87 ml, 24.73 mmol) was added dropwise to the solution. While being allowed to wa... | COC(=O)C(C)(C)CON1C(=O)c2ccccc2C1=O | null | 33.6 | null |
1,231,987 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [C:1]([N:4]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C@@H:11]2[C:6]([C:7]3[CH:23]=[C:22]([O:24]C)[CH:21]=[CH:20][C:8]=3[CH2:9][CH2:10]2)=[N:5]1)(=[O:3])[CH3:2].B(Br)(Br)Br.Cl>ClCCl>[C:1]([N:4]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C@@H:11]2[C:6]([C:7]3[CH:23]=[C:22](... | COc1ccc2c(c1)C1=NN(C(C)=O)[C@@H](c3ccc(O)cc3)[C@H]1CC2 | null | null | BrB(Br)Br | Cl | 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 | 1 | To a solution of (175) (0.100 g, 0.28 mmol) under an argon atmosphere in dichloromethane (5 mL) was added BBr3 (1.0 mL, 1.0 M solution in dichloromethane) at −78° C. The reaction mixture was stirred at room temperature for 1 h and then poured into an ice cold solution of HCl (1.0 N). The mixture was extracted in ethyl ... | CC(=O)N1N=C2c3cc(O)ccc3CC[C@@H]2[C@@H]1c1ccc(O)cc1 | null | null | null |
217,027 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[NH:18][C:17](=[O:19])[NH:16][C:12]3=[N:13][C:14]=2[CH3:15])=[CH:5][CH:4]=1.[C:20](Cl)(=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24]>>[CH2:21]([C:20]([NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[NH:18][C:17](=[O:19])[NH:16][C:12]3=[N:13][C:14]=2[CH3:15])=[CH:5]... | CCCCC(=O)Cl | Cc1nc2[nH]c(=O)[nH]c2cc1-c1ccc(N)cc1 | 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 | [I; Ar 4-CH3 (CH2)3CONHC6H4, R1 and R3H, R5 =CH3 ]was prepared from 3 g 6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one hydrochloride and 1.86 ml valeryl chloride according to the procedure of Example 7, and was obtained (1.16 g) as a colorless solid, m.p. above 300° C. when recrystallized from et... | CCCCC(=O)Nc1ccc(-c2cc3[nH]c(=O)[nH]c3nc2C)cc1 | null | null | null |
476,737 | ord_dataset-d56f0a7ec215495c92e641d9fa932d28 | null | 2000-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.B(F)(F)F.C[CH2:18][O:19][CH2:20][CH3:21]>C(#N)C>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:3]2[C:4]3[C:21](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:20]([O:19][CH3:18])=[CH:11][CH:12]=2)=[CH:5][CH:4]=1 | CCOCC | COc1cccc2ccccc12 | null | FB(F)F | 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 | 25 | 1.5 | In synthetic route `A3`, 1-methoxynaphthalene and a solution of tris(trifluoroacetato)thallium[III] in acetonitrile are charged to a reaction vessel. Boron trifluoride etherate is added and the reaction mixture stirred at room temperature for between approximately 1-2 h to provide the intermediate 4,4'-dimethoxy-1,1'-b... | COc1ccc(-c2ccc(OC)c3ccccc23)c2ccccc12 | null | null | null |
150,878 | ord_dataset-b9a9e369e9da4413999591aa08f4c3e3 | null | 1986-01-01T00:11:00 | true | [C:1]1([C:7]2[O:12][C:11](=O)[NH:10][C:9](=[O:14])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][NH2:16]>>[CH3:15][N:16]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][C:9](=[O:14])[NH:10][C:11]1=[O:12] | CN | O=c1cc(-c2ccccc2)oc(=O)[nH]1 | 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 | 25 | null | To 189 mg (1 mM) of 6-phenyl-1,3-oxazine-2,4-dione from Preparation Ia(1) is added 10 ml of a 40 percent aqueous CH3NH2 solution. The reaction mixture is allowed to heat at reflux for 18 hours. The resulting solution is cooled to room temperature and the precipitate filtered, washed well with water, and dried at 60° C.... | Cn1c(-c2ccccc2)cc(=O)[nH]c1=O | null | null | null |
1,501,187 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].CC1(C)C(C)(C)OB([C:21]2[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24])O1.C1(C)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C... | COC(=O)c1ccc(Br)c(C)c1 | CCOC(=O)c1ccccc1B1OC(C)(C)C(C)(C)O1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=P([O-])([O-])[O-] | [K+] | 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 | 25 | null | Under a nitrogen atmosphere, to a mixture of methyl 4-bromo-3-methylbenzoate (2.291 g), ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (3.313 g), toluene (20 ml), water (10 ml) and tripotassium phosphate (4.246 g) was added tetrakis(triphenylphosphine)palladium(0) (0.578 g) at room temperature, and the m... | CCOC(=O)c1ccccc1-c1ccc(C(=O)OC)cc1C | null | 80.6 | null |
1,167,274 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:34]=[CH:35][C:36]([O:42][CH2:43][C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)=[C:37]([NH:39][CH:40]=[O:41])[CH:38]=4)[O:25][Si](C(C)(C)C)(C)C)=[CH:16][CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2... | CC(C)(C)[Si](C)(C)O[C@@H](CNCCc1ccc(OCCC23CC4CC(CC(C4)C2)C3)cc1)c1ccc(OCc2ccccc2)c(NC=O)c1 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | 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 | To a solution of Intermediate 25 (1.23 g, 1.44 mmol) in tetrahydrofuran (20 mL) was added tetrabutylammonium fluoride on silica gel (1-1.5 mmol/g, 2 g). The reaction mixture was stirred first at room temperature overnight and then at 45° C. for 3 hours. Silica was filtrated and the solvent was removed under reduced pre... | O=CNc1cc([C@@H](O)CNCCc2ccc(OCCC34CC5CC(CC(C5)C3)C4)cc2)ccc1OCc1ccccc1 | null | 44 | null |
588,383 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [CH2:1]=O.[NH:3]1[CH2:8][CH2:7][CH:6]([O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH2:5][CH2:4]1>>[CH3:1][N:3]1[CH2:4][CH2:5][CH:6]([O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH2:7][CH2:8]1 | COC(=O)c1ccc(OC2CCNCC2)cc1 | 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 | Prepared using essentially the same procedure used in reference example 114a except using formaldehyde and Methyl 4-(piperidin-4-yloxy)-benzoate (reference example 123) as substrates. 1H NMR (CDCl3): d 8.01 (d, 2H), 6.91 (d, 2H), 4.80 (s, 1H), 3.89 (s, 3H), 3.35 (brd, 2H), 3.13 (q, 2H), 2.80 (d, 3H), 2.65 (t, 2H), 2.18... | COC(=O)c1ccc(OC2CCN(C)CC2)cc1 | null | null | null |
549,721 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [C:1]([CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[OH:8][C@H:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11] | COC(=O)CC(=O)c1ccccc1 | null | null | null | null | 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 | null | In a 1 liter autoclave was charged a mixture of 0.84 g of (1.0 mmol) of Ru2Cl4((R)-Tol-BINAP)2.NET3, 178 g (1.00 mol) of methyl benzoylacetate, and 500 ml of methanol, and the mixture was stirred at 50° C. under a hydrogen pressure of 1000 kPa for 16 hours. The solvent was evaporated under reduced pressure, and the res... | COC(=O)C[C@H](O)c1ccccc1 | null | 94.9 | null |
362,419 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]O.[Cl:21]C1C=C2C(C=CC(COC3C=CC(CO)=CC=3)=N2)=CC=1>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH... | OCc1cccc(OCc2ccc3ccccc3n2)c1 | OCc1ccc(OCc2ccc3ccc(Cl)cc3n2)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 procedure from Example 6, part B was used except 3-(quinolin-2-ylmethoxy)benzyl alcohol was substituted for 4-(7-chloroquinolin-2-ylmethoxy)benzyl alcohol. The intermediate was obtained in 72% yield: mp 39°-43° C. | ClCc1cccc(OCc2ccc3ccccc3n2)c1 | null | 72 | null |
685,658 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[NH:19][C:20](=[O:37])[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([CH3:36])[CH:31]=2)[CH:25]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:14][C:12]1[C:11]([C:15]([F:18])([F:17])[F:16])=... | Cc1cc(-c2cccc(C(=O)CC(=O)Nc3cc(C(F)(F)F)c(Cl)cc3NC(=O)OC(C)(C)C)c2)ccn1 | null | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (5-chloro-2-{3-[3-(2-methyl-pyridin-4-yl)-phenyl]-3-oxo-propionylamino}-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example M75) (0.34 g, 0.62 mmol) by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as an off-white solid (222 mg, 83%). | Cc1cc(-c2cccc(C3=Nc4cc(Cl)c(C(F)(F)F)cc4NC(=O)C3)c2)ccn1 | null | null | null |
1,358,829 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)([CH2:16][C:17]([OH:20])([CH3:19])[CH3:18])[O:12][C:11]2=[O:28])[CH3:9])=[CH:4][CH:3]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C@:13]2([CH2:16][C:17]... | C[C@@H](c1ccc(Br)cc1)N1CC[C@](CC(C)(C)O)(c2ccc(F)cc2)OC1=O | OB(O)c1ccccn1 | 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 (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxy-2-methylpropyl)-1,3-oxazinan-2-one and pyridine-2-boronic acid following a procedure analogous to that described in Example 75 Step 1. LC-MS Method 2 tR=1.049 min, m/z=391; 1H NMR (CDCl3) 1.06-1.19 (d, 6H), 1.50 (s, ... | C[C@@H](c1ccc(-c2ccccn2)cc1)N1CC[C@](CC(C)(C)O)(c2ccc(F)cc2)OC1=O | null | null | null |
152,100 | ord_dataset-5944a40bb4504bbe8185cfdf2a811d03 | null | 1987-01-01T00:01:00 | true | [ClH:1].Br[C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([C:13]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[O:14])[CH:12]=1)[O:9][C:8]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[C:7]([CH3:30])[C:6]2=[O:31]>>[Cl:1][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([C:13]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][... | Cc1c(-c2ccccc2)oc2c(C(=O)OCCN3CCOCC3)cc(Br)cc2c1=O | 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 | null | null | The procedure of Example 13 was repeated with the exception of using 37.3 g (0.10 mole) of methyl 6-bromo-3-methylflavone-8-carboxylate in place of methyl 6-chloro-3-methylflavone-8-carboxylate, giving 44 g (93.2%) of crystals. The hydrochloride of the product melts at 205.0° to 208.0° C. The crystals were found to be ... | Cc1c(-c2ccccc2)oc2c(C(=O)OCCN3CCOCC3)cc(Cl)cc2c1=O | null | null | null |
727,474 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:3].[ClH:11]>CCCCCCC>[ClH:11].[CH3:1][NH+:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:3] | CN(C)Cc1ccccc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | 12.12 g of N,N-dimethylbenzylamine and 400 ml of heptane were placed under argon in a 500 ml three-necked flask fitted with internal thermometer and gas inlet stopcock. HCl gas from a gas generation apparatus was passed into this reaction mixture for 1 hour. The N,N-dimethylbenzylammonium hydrochloride formed was separ... | C[NH+](C)Cc1ccccc1 | null | null | null |
1,455,149 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[O:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)O1.[F:22][C:23]1[C:24](C2C=CC(OC[C@H]3CC[C@H](OC4CCCCO4)CC3)=CC=2)=[CH:25][C:26](=[O:42])[N:27]([CH2:29][CH2:30][C@@:31]([CH3:41])([S:37]([CH3:40])(=[O:39])=[O:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:28]=1>>[F... | CC1(C)OB(c2cccc(Oc3nccs3)c2)OC1(C)C | CCOC(=O)[C@@](C)(CCn1cc(F)c(-c2ccc(OC[C@H]3CC[C@H](OC4CCCCO4)CC3)cc2)cc1=O)S(C)(=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 | null | null | The title compound (534 mg) was prepared as a crude brown oil from 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1,3-thiazole (1.33 g, 4.39 mmol) and T2 (400 mg, 0.90 mmol) using a procedure analogous to that described for ethyl (2R)-4-[5-fluoro-2-oxo-4-(4-{[trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]... | CCOC(=O)[C@@](C)(CCn1cc(F)c(-c2cccc(Oc3nccs3)c2)cc1=O)S(C)(=O)=O | null | null | null |
875,062 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | [F:1][C:2]1[C:9]([F:10])=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:19]([O:23][C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=... | N#Cc1ccc(OS(=O)(=O)C(F)(F)F)c(F)c1F | CC(C)(C)OC(=O)Nc1ccc(B(O)O)cc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | 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 | 90 | 3 | A solution of 2,3-difluoro-4-trifluoromethylsulfonyloxybenzonitrile in 60 mL of dioxane is admixed under an argon atmosphere with 1.24 g of 4-(tert-butyloxycarbonylamino)phenylboronic acid. A solution of 1.03 g of sodium carbonate in 15 mL of water is added, followed by 0.48 g of tetrakistriphenylphosphinepalladium. Th... | CC(C)(C)OC(=O)Nc1ccc(-c2ccc(C#N)c(F)c2F)cc1 | null | null | null |
754,762 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [C:1]1([CH3:8])[CH:6]=[CH:5][C:4](Br)=[CH:3][CH:2]=1.[Mg].[CH:10]12[O:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]2>C1COCC1>[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])=[CH:3][CH:2]=1 | Cc1ccc(Br)cc1 | C1CCC2OC2C1 | null | [Mg] | 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 | -20 | 0.17 | To a solution of p-tolylbromide (17.1 g, 100 mmol) in dry THF (100 mL) was added magnesium (2.43 g, 100 mmol) and then the resulting mixture was cooled to −20° C. and (CuBr-dimethylsulfide complex (2.0 g, 10 mmol) was added and the mixture stirred at −20° C. for 10 min. Then a solution of cyclohexene oxide (10 mL, 100 ... | Cc1ccc(C2CCCCC2=O)cc1 | null | 52.6 | null |
1,315,975 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5](=[N:7][OH:8])[NH2:6].Cl.[C:14](Cl)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.N>>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:14]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[F:12] | NC(=NO)c1ccc(F)c(F)c1 | O=C(Cl)c1cccnc1 | null | Cl | N | 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 according to the procedure of Example 1 using 3,4-difluoro-N′-hydroxybenzimidamide (Tyger Scientific) and nicotinoyl chloride hydrochloride (Aldrich). 1H NMR (300 MHz, DMSO-d6) δ 7.74 (dd, J=7.5, 4.4 Hz, 1 H), 8.60 (dt, J=7.8, 2.1 Hz, 1 H), 8.93 (dd, J=4.8, 1.6 Hz, 1 H), 9.38 (dd, J=2.2,... | Fc1ccc(-c2noc(-c3cccnc3)n2)cc1F | null | null | null |
1,559,779 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [OH:1][CH2:2][CH2:3][N:4]([CH3:18])[C:5](=[O:17])[NH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[CH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:1][CH2:2][CH2:3][N:4]([CH3:18])[C:5]([NH:6][C:7]1[CH:16]=[CH:15][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1)=[O:17] | COC(=O)c1ccc(NC(=O)N(C)CCO)cc1 | null | null | [Al+3] | [H-] | [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 | 18 | To a cooled (−78° C.) solution of methyl 4-(3-(2-hydroxyethyl)-3-methylureido)benzoate (2.02 g, 8.00 mmol) in THF (80 mL) was added a solution of lithium aluminium hydride (2.0 M solution in THF, 6.0 mL, 12.0 mmol). After 20 minutes the coolant was removed and the reaction mixture stirred at RT for 18 h. The reaction m... | CN(CCO)C(=O)Nc1ccc(CO)cc1 | null | 60.8 | null |
1,520,115 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [Na+].[Cl:2][C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6](=[CH:10][CH:11]=1)[C:7]([O-:9])=O>S(Cl)(Cl)=O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:12](=[O:13])[O:14][C:7](=[O:9])[C:6]2=[CH:10][CH:11]=1 | O=C([O-])c1ccc(Cl)cc1C(=O)O | null | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | The mixture of commercial 4-chlorophthalic acid monosodium salt (40 g) and thionyl chloride (50 ml) was stirred under reflux for 2 h. From the resulting viscous mass all volatiles were removed at the water aspirator. The residue was heated with benzene (150 ml) and the still hot slurry was filtered by suction. The filt... | O=C1OC(=O)c2cc(Cl)ccc21 | null | 64.3 | null |
1,226,373 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.Br[C:12]1[CH:13]=[CH:14][C:15]([F:19])=[C:16]([CH3:18])[CH:17]=1>>[F:19][C:15]1[CH:14]=[CH:13][C:12]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]2)=[CH:17][C:16]=1[CH3:18] | COC(=O)C1CCNCC1 | Cc1cc(Br)ccc1F | 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 | starting with 10.6 g (74.0 mmol) of methyl piperidine-4-carboxylate and 4.67 g (24.7 mmol) of 5-bromo-2-fluorotoluene, the general procedure [E] gives 2.74 g (40% of theory) of product. | COC(=O)C1CCN(c2ccc(F)c(C)c2)CC1 | null | null | null |
1,752,225 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]2=[O:20].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1>>[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([C:11]=2[CH3:12])=[C:9]([CH:13]2[CH2:15][CH2:14]2)[CH:8]... | OB(O)c1cccnc1 | COC(=O)c1cc(C2CC2)c2c(C)c(Cl)ccn2c1=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 | Methyl 8-(pyridin-3-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A from methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol) and pyridin-3-yl-boronic acid (63 mg, 0.51 mmol). Purification by flash silica column chromat... | COC(=O)c1cc(C2CC2)c2c(C)c(-c3cccnc3)ccn2c1=O | null | 88 | null |
639,234 | ord_dataset-1c0bae7388cf460091d56129e95b3145 | null | 2004-01-01T00:06:00 | true | [F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[NH:24]1[C:28]2[CH2:29][CH2:30][CH2:31][C:27]=2[C:26]([NH2:32])=[N:25]1>O1CCCC1.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]([NH:32][C:26]3[C:27]4[CH2:31][C... | Nc1n[nH]c2c1CCC2 | O=C(O)Cc1ccc(-c2cccc(F)c2)cc1 | null | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | 230 mg of 2-(3′-fluoro-biphenyl-4-yl)-acetic acid is dissolved in 5 ml of tetrahydrofuran, mixed with 0.11 ml of oxalyl chloride and one drop of dimethylformamide, and stirred for 2 hours at room temperature. 62 mg of 1,4,5,6-tetrahydro-cyclopentapyrazol-3-yl-amine is added to this solution. The mixture is stirred for ... | O=C(Cc1ccc(-c2cccc(F)c2)cc1)Nc1n[nH]c2c1CCC2 | null | null | null |
865,168 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][CH:8]=1)[CH3:2].Cl[CH2:20][C:21]1[C:22]([CH:37]2[CH2:39][CH2:38]2)=[N:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[N:25][CH:26]=1>>[CH2:1]([O:3][C:4](=[O:18])[C... | FC(F)(F)c1ccc(-c2ncc(CCl)c(C3CC3)n2)cc1 | CCOC(=O)CCc1ccc(O)c2ccccc12 | 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] In analogy to the procedures described in example 5C] and 5D], 3-(4-hydroxy-naphthalen-1-yl)-propionic acid ethyl ester [Helvetica Chimica Acta (2001), 84(8), 2198-2211] was reacted with 5-chloromethyl-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (example 9E]) to give 3-{4-[4-cyclopropyl-2-(4-trifluoromethy... | CCOC(=O)CCc1ccc(OCc2cnc(-c3ccc(C(F)(F)F)cc3)nc2C2CC2)c2ccccc12 | null | null | null |
1,730,454 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [CH:1]1([CH2:4][O:5][C:6]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]2)[CH2:3][CH2:2]1.[ClH:24]>C(OCC)(=O)C>[ClH:24].[CH:1]1([CH2:4][O:5][C:6]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH2:7][NH:8][CH2:9]2)[CH2:2][CH2:3]1 | Cc1ccccc1C1(OCC2CC2)CN(C(=O)OC(C)(C)C)C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 2.8 g (9.0 mmol) of tert-butyl 3-cyclopropylmethoxy-3-o-tolylazetidine-1-carboxylate are placed in 40 ml of a 3M solution of hydrogen chloride in ethyl acetate and are stirred at room temperature for 1 hour 30 minutes. The reaction medium is concentrated under a stream of nitrogen and then taken up in a 50/50 heptane/e... | Cc1ccccc1C1(OCC2CC2)CNC1 | null | 96 | null |
1,369,086 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[NH2:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23](F)[C:20]=1[C:21]#[N:22]>>[NH2:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([O:15][CH2:14][CH:11]2[CH2:12][CH2:13][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2... | COc1ccc(CN2CCC(CO)CC2)cc1 | N#Cc1c(N)cccc1F | 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 as in Example 22b from (1-(4-methoxybenzyl)piperidin-4-yl)methanol (Example 125c) and 2-amino-6-fluorobenzonitrile as an orange solid (19%). MS 352 (MH+). | COc1ccc(CN2CCC(COc3cccc(N)c3C#N)CC2)cc1 | null | null | null |
364,321 | ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | null | 1997-01-01T00:05:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][C:12]2=[O:15])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>CO.O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][CH:12]2[OH:15])=[CH:7][CH:6]=1)=[O:4] | COC(=O)c1ccc2c(c1)C(=O)CCC2 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 5 | null | In a mixture of 150 ml of methanol and 50 ml of tetrahydrofuran, 24.1 g of 7-methoxycarbonyl-3,4-dihydro-(2H)-1-naphthalenone was dissolved and 5 g of sodium borohydride was added by portions with ice cooling. The mixture was stirred at 5° C. for an hour and successively the solvent was distilled off under reduced pres... | COC(=O)c1ccc2c(c1)C(O)CCC2 | null | null | null |
1,696,250 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | C(O[C:6](=[O:15])[NH:7][CH2:8][CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])(C)(C)C.FC(F)(F)C(O)=O.COC([C:27]1[C:28]([OH:51])=[C:29]2[C:34](=[CH:35][N:36]=1)[N:33]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32](=[O:44])[C:31]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[CH:30]2)=O>C(Cl)Cl>[CH3:14][S... | CC(C)(C)OC(=O)NCCNS(C)(=O)=O | COC(=O)c1ncc2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | 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 | 25 | 2 | (2-Methanesulfonylamino-ethyl)-carbamic acid tert-butyl ester (94 mg, 0.38 mmol) was dissolved in CH2Cl2 (2 mL). Trifluoroacetic acid (1 mL) was added, and the mixture was stirred at r.t. for 2 h. Solvent and excess TFA were removed by evaporation, and the residue was taken up in EtOH (3 mL). NaOMe was added with vigor... | CS(=O)(=O)NCCNC(=O)c1ncc2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | null | 33.1 | null |
1,649,337 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[CH:4][C:3]=1[CH3:10].C([N:19]=[C:20]=[S:21])(=O)C1C=CC=CC=1.[OH-].[Na+]>CC(C)=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][C:20]([NH2:19])=[S:21])=[CH:4][C:3]=1[CH3:10] | O=C(N=C=S)c1ccccc1 | Cc1cc(N)cc(C)c1Br | null | [Na+] | [OH-] | 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 | 50 | 12 | A solution of 4-bromo-3,5-dimethyl-phenylamine (200 mg) and benzoyl isothiocyanate (0.14 ml) in acetone (2 ml) was heated under reflux for 30 minutes. After cooling the reaction solution, a 1 N aqueous sodium hydroxide solution (2.19 ml) was added and the mixture was stirred at 50° C. for 12 hours. The mixture was extr... | Cc1cc(NC(N)=S)cc(C)c1Br | null | 57 | null |
1,293,617 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | CC(C)(OC([NH:7][C@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=1)[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]2[CH:18]=[CH:19][N:20]=[C:14]2[CH2:13]1)=[O:11])=O)C.[ClH:31]>CO>[ClH:31].[ClH:31].[NH2:7][C@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=1)[CH2:9][C:10]([N:1... | CC(C)(C)OC(=O)N[C@@H](CC(=O)N1CCn2ccnc2C1)Cc1ccc(F)c(F)c1 | null | null | Cl | null | 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 | null | The title compound was prepared from 7-[(3R)-3-[(1,1-dimethylethoxycarbonyl)-amino]-4-(3,4-difluorophenyl)butanoyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (72 mg, 0.171 mmol, from Step C), in 1.5 mL of methanol saturated with hydrogen chloride, using a procedure analogous to that described in Example 1, Step D. Conce... | N[C@@H](CC(=O)N1CCn2ccnc2C1)Cc1ccc(F)c(F)c1 | null | null | null |
463,431 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [F:1][C:2]([F:33])([C:23]([F:32])([F:31])[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14].[CH2:34]=O.Cl>C(O)=O>[F:1][C:2]([F:33])([C:23]([F:31])([F:32])[C:24]([F:29])([F:30])[... | FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CCCNCCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F | C=O | null | Cl | null | 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 | null | 90 | null | A solution of bis(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)amine (3.0 g) and formic acid (90%, 1.5 g) was cooled in an ice-water bath and 8 ml of formaldehyde (37% weight) was added. The solution was slowly heated to 90° C. and maintained overnight. (Foaming and gas evolution at 60-75° C.) Concentrated hydrochloric acid (1 m... | CN(CCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F)CCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F | null | 88 | null |
1,158,137 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].[N-:13]=[N+]=[N-].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CC#N.O>[N+:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][NH2:13])([O-:12])=[O:11] | O=[N+]([O-])c1ccccc1CCBr | [N-]=[N+]=[N-] | null | [Na+] | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 25 | 16 | To a solution of 1-(2-Bromoethyl)-2-nitrobenzene (6.96 g, 30.5 mmol) in CH3CN was added a solution of NaN3 (6 g, 91.6 mmol) in water (20 ml) and the reaction mixture was refluxed for 20 hours. The solution was cooled and extracted with DCM (3×). The organics were combined, washed with brine, dried (MgSO4) and evaporate... | NCCc1ccccc1[N+](=O)[O-] | null | null | null |
1,193,053 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [CH3:1][O:2][C:3](=[O:22])[C@@H:4]([NH:14]C(OC(C)(C)C)=O)[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:22])[C@@H:4]([NH2:14])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1 | COC(=O)[C@H](CCOc1ccccc1)NC(=O)OC(C)(C)C | null | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | 16 | To a solution of (S)-2-tert-butoxycarbonylamino-4-phenoxy-butyric acid methyl ester (1.15 g) in dichloromethane (3 ml) was added under an argon atmosphere trifluoroacetic acid (4.2 ml). The mixture was stirred for 16 h. The mixture was concentrated. The residue was treated with sodium bicarbonate solution until the pH ... | COC(=O)[C@@H](N)CCOc1ccccc1 | null | null | null |
603,238 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [CH:1]([C:3]1[NH:4][C:5]([CH3:11])=[CH:6][C:7]=1[C:8]([OH:10])=O)=[O:2].[NH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[N:15]1([CH2:14][CH2:13][NH:12][C:8]([C:7]2[CH:6]=[C:5]([CH3:11])[NH:4][C:3]=2[CH:1]=[O:2])=[O:10])[CH2:19][CH2:18][CH2:17][CH2:16]1 | NCCN1CCCC1 | Cc1cc(C(=O)O)c(C=O)[nH]1 | 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 | 2-Formyl-5-methyl-1H-pyrrole-3-carboxylic acid (3.0 g, 19.6 mmol) reacted with 1-(2-aminoethyl)pyrrolidine (2.73 mL, 21.5 mmol) to give 3.71 g (76%) of 2-formyl-5-methyl-1H-pyrrole-3-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide. | Cc1cc(C(=O)NCCN2CCCC2)c(C=O)[nH]1 | null | 75.9 | null |
499,152 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | O.[ClH:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([OH:11])=[O:10].[CH3:12]O>S(Cl)(Cl)=O>[ClH:2].[Cl:2][C:6]1[CH:7]=[CH:8][N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=1 | O=C(O)c1ccccn1 | CO | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | O | null | null | null | null | null | null | null | null | null | 25 | null | H2O (18 mL) was added dropwise to a stirred suspension of picolinic acid hydrochloride, compound 1 (157.9 g, 1.0 mol) in thionyl chloride (400 mL). The resulting mixture was heated under reflux for 4 days giving a clear orange solution. After cooling to ambient temperature, the solution was concentrated to a syrup and ... | COC(=O)c1cc(Cl)ccn1 | null | 85 | null |
43,549 | ord_dataset-ff0bcb6c2300494cbdf16005ad32ad5f | null | 1978-01-01T00:08:00 | true | [NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][C:3]=1C(O)=O.[OH-].[Na+].[Na]>O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][CH:3]=1 | Nc1c(C(=O)O)cc(O)c2c1C(=O)c1ccccc1C2=O | null | null | [Na+] | [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 | 25 | 2 | 1-Amino-4-hydroxyanthraquinone-2-carboxylic acid (31.1 grams, 0.11 mole) was dissolved in 2000 ml. of water and 50 ml. of 10 M sodium hydroxide solution. The mixture was heated on a steam bath to 90°-100° C., and 40 g (0.23 mole) sodium hydro ulfite was added. Heating was continued with stirring for 2 hours, after whic... | Nc1ccc(O)c2c1C(=O)c1ccccc1C2=O | null | 99.6 | null |
685,455 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[NH2:19])([CH3:4])([CH3:3])[CH3:2].C([O:25][C:26](=O)[CH2:27][C:28](=[O:41])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)[CH:30]=1)(C)(C)C>>[C:1]([O:5][C:6](=[O:20])[NH:7... | Cc1cc(NC(=O)OC(C)(C)C)c(N)cc1C(F)(F)F | CC(C)(C)OC(=O)CC(=O)c1cccc(-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-5-methyl-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J20) (218 mg, 0.75 mmol) and 3-oxo-3-(3-pyridin-3-yl-phenyl)-propionic acid tert-butyl ester (Example K1) (223 mg, 0.75 mmol) according to the general procedure M. Obtained as a light yellow foam (27... | Cc1cc(NC(=O)OC(C)(C)C)c(NC(=O)CC(=O)c2cccc(-c3cccnc3)c2)cc1C(F)(F)F | null | null | null |
520,128 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7](C(OCC)=O)[C:6]=1[C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:3])[CH3:2].[K+].[Br-]>>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:3]... | CCOC(=O)n1c(C(=O)c2ccccc2)c(NC(C)=O)c2ccccc21 | null | null | [Br-] | [K+] | 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 according to the procedure described in step 2 of Example 2 (Method A) from 3-acetylamino-2-benzoyl-1-(ethoxycarbonyl)indole (step 1). 1H-NMR (CDCl3) δ: 9.78 (1H, br s), 8.24 (1H, d, J=8 Hz), 8.22 (1H, br s), 7.82 (2H, d, J=8 Hz), 7.64-7.52 (3H, m), 7.42-7.25 (2H, m), 7.16 (1H, t, J=8 Hz... | CC(=O)Nc1c(C(=O)c2ccccc2)[nH]c2ccccc12 | null | null | null |
429,111 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[OH-].[Na+].[C:15](#[N:18])[CH:16]=[CH2:17]>C1(C)C=CC=CC=1>[OH:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[C:8]=1[CH2:17][CH2:16][C:15]#[N:18] | C=CC#N | Oc1ccc2cc(Br)ccc2c1 | null | [Na+] | [OH-] | 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 | 65 | 0.5 | To 44.8 g of 6-bromo-2-naphthol were added 120 ml of toluene and 8.8 g of sodium hydroxide, followed by stirring at 65° C. for 30 minutes. Then, thereto was added dropwise 11.4 g of acrylonitrile at 80° C., followed by stirring at the same temperature for 3.5 hours. After left for cooling, the toluene layer was decante... | N#CCCc1c(O)ccc2cc(Br)ccc12 | null | 55.4 | null |
206,311 | ord_dataset-dd1de64954674e17b4b690cac09dc67b | null | 1990-01-01T00:04:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:14][CH2:15]CCCN>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:15][Cl:14])=[O:7])([CH3:2])([CH3:3])[CH3:4] | CC(C)(C)OC(=O)NCCCCl | NCCCCCl | 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 | This compound, employed as the starting material in example 2, is prepared by following substantially the same procedure described above under (a) but using 4-chloro-butylamine hydrochloride instead of 3-chloro-propylamine hydrochloride. | CC(C)(C)OC(=O)NCCCCCl | null | null | null |
67,916 | ord_dataset-dabcd66611f34094b1baca0095305a66 | null | 1980-01-01T00:07:00 | true | [NH2:1][C:2]1[C:3](=[O:12])[O:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(O[CH:16]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>>[CH2:21]([O:20][C:18](=[O:19])[C:17](=[CH:16][NH:1][C:2]1[C:3](=[O:12])[O:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[CH:11]=1)[C:23]([O:25]... | CCOC=C(C(=O)OCC)C(=O)OCC | Nc1cc2ccccc2oc1=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 | 120 | null | A mixture of 3-aminocoumarin (30.0 g, 0.186 mole) and diethyl ethoxymethylenemalonate (75.0 g, 0.347 mole) is heated at 120° C. for 4 hours under nitrogen. The reaction mixture is cooled and triturated with hexane. The product is filtered off and washed with hexane. Recrystallization from ethyl acetate gives white crys... | CCOC(=O)C(=CNc1cc2ccccc2oc1=O)C(=O)OCC | null | 89.2 | null |
1,541,471 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [NH:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1.[CH3:23][S:24][CH2:25][CH2:26]/[CH:27]=[CH:28]/[C:29]#[N:30].C1CCN2C(=NCCC2)CC1.C(#N)C>>[CH3:23][S:24][CH2:25][CH2:26][CH:27]([N:1]1[CH:5]=[C:4]([C:6]2[C:7]3... | CSCC/C=C/C#N | C[Si](C)(C)CCOCn1ccc2c(-c3cn[nH]c3)ncnc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | 25 | 120 | A mixture of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (0.30 g, 0.00095 mol), (2E)-5-(methylthio)pent-2-enenitrile (0.28 g, 0.0016 mol) and DBU (45 μL, 0.00030 mol) in ACN (3 mL, 0.06 mol) was stirred at rt for 5 days. The solvent was removed by rotary evaporation to give an or... | CSCCC(CC#N)n1cc(-c2ncnc3c2ccn3COCC[Si](C)(C)C)cn1 | null | 83.2 | null |
391,431 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | [CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[CH:10]=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.CN(C)[N:15]=[CH:16][C:17]([F:19])=[CH2:18]>C(Cl)(Cl)Cl>[F:19][C:17]1[CH2:18][C:10]2[C:11](=[O:12])[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7](=[O:8])[C:9]=2[NH:15][CH:16]=1 | O=C1C=CC(=O)c2ccccc21 | C=C(F)C=NN(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A solution of naphthoquinone (632 mg, 4 mmol) and 2-fluoro-2-propenal N,N-dimethylhydrazone was refluxed for 22 hours in dry chloroform (15 ml.) Another portion of naphthoquinone (0.41 g, 2.59 mmol) was added and the reflux continued for 3 more hours. After the solvent was evaporated at reduced pressure, silica gel col... | O=C1C2=C(NC=C(F)C2)C(=O)c2ccccc21 | null | 5 | null |
839,376 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:5]=[CH:6][C:7](OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH:27][C:28]1[CH:37]=[C:36]2[C:31]([C:32](=[O:44])[CH2:33][CH:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[O:35]2)=[CH:30][CH:29]=1>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:27][C:28]2[CH:37]=[C:36]3[C:31]([C:32](=[O:44])[... | O=[N+]([O-])c1ccc(Oc2ccc3c(c2)CCC(c2ccccc2)O3)nc1 | O=C1CC(c2ccccc2)Oc2cc(O)ccc21 | 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 | 7-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-one was prepared as described for 5-Nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) using 150 mg of 7-hydroxyflavanone. 1H NMR (400 MHz, d6-DMSO) δ: 9.07 (d, 1H, J 2.8 Hz), 8.67 (dd, 1H, J 9.0, 2.8 Hz), 7.89 (d, 1H, 8.6 Hz), 7.60-7.35 (m, 6H), 7.04 (d, 1H, 2.1 Hz),... | O=C1CC(c2ccccc2)Oc2cc(Oc3ccc([N+](=O)[O-])cn3)ccc21 | null | null | null |
539,016 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:13][O:14][N:15]=[C:16]([C:32]1[O:33][CH2:34][CH2:35][N:36]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23]CC1C=CC(Cl)=CC=1>O>[CH3:13][O:14][N:15]=[C:16]([C:32]1[O:33][CH2:34][CH2:35][N:36]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23] | CON=C(C1=NCCO1)c1ccccc1OCc1ccc(Cl)cc1 | null | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | COc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | Anisole (152 ml) and aluminium chloride (16.3 g, 122 mmol) were added to 2-(4-chlorobenzyloxy)phenyl 2-oxazolin-2-yl ketone O-methyloxime (19.08 g, 55.3 mmol), and the mixture was stirred under ice-cooling for 1.5 hours. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with ethy... | CON=C(C1=NCCO1)c1ccccc1O | null | 56 | null |
1,393,057 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [F:1][C:2]1([F:47])[CH2:5][CH:4]([NH:6][C:7]([NH:9][C@:10]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[C:34](/[CH:39]=C/C3C=CC=CC=3)[CH:33]=2)([C:18]2[CH:23]=[C:22]([O:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])[CH:21]=[C:20]([F:31])[CH:19]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])[CH2:3]1.C[N+]1([... | O=C(NC1CC(F)(F)C1)N[C@@](Cc1ccccc1)(c1cc(F)cc(OC(F)(F)C(F)F)c1)c1ccc(F)c(/C=C/c2ccccc2)c1 | C[N+]1([O-])CCOCC1 | 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 | null | null | To a solution of (R,E)-1-(3,3-difluorocyclobutyl)-3-(1-(4-fluoro-3-styrylphenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)urea (509 mg, 0.8 mmol) in DCM (10 ml) at 0° C. was added 4-methylmorpholine N-oxide (104 mg, 0.8 mmol). Ozone was bubbled through the resulting yellow solution for 10 min. The... | O=Cc1cc([C@@](Cc2ccccc2)(NC(=O)NC2CC(F)(F)C2)c2cc(F)cc(OC(F)(F)C(F)F)c2)ccc1F | null | 22.6 | null |
1,534,411 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [N:1]12[CH2:8][CH2:7]C([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:9](O)=O.S(Cl)(Cl)=O.[CH3:16]N(C)C=O>>[CH2:8]([N:1]([CH:2]([CH3:3])[CH3:9])[CH:6]([CH3:5])[CH3:16])[CH3:7] | O=C(O)C1CC2CCN1CC2 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 15 | A mixture of 1-azabicyclo[2.2.2]octane-2-carboxylic acid (488 mg), thionyl chloride (5 mL) and N,N-dimethylformamide (23 mg) was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (5 mL). A mixture of methyl 3-amino-5-[1-... | CCN(C(C)C)C(C)C | null | null | null |
1,195,432 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [CH3:1][C:2]1([CH3:25])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([C:14](=[O:24])[CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1.O>CCO.[Fe]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:25])([CH3:1])[CH2:3][N:4]2[C:14](=[O:24])[CH2:15][NH:16][C:17]([O:19][C:20]([CH3:2... | CC(C)(C)OC(=O)NCC(=O)N1CC(C)(C)c2ccc([N+](=O)[O-])cc21 | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 80 | 8 | 1-(3,3-Dimethyl-6-nitro-2,3-dihydro-indol-1-yl)-2-(N-Boc-amino)-ethanone (3.9 g) was dissolved in EtOH (30 ml) and Fe powder (3.1 g) NH4Cl (299 mg) and H2O (5 ml) were added. The reaction was stirred at 80° C. overnight. The reaction was filtered through Celite® and evaporated off the MeOH. The residue was partitioned ... | CC(C)(C)OC(=O)NCC(=O)N1CC(C)(C)c2ccc(N)cc21 | null | null | null |
920,699 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]=[CH2:19])[C:13](=[O:20])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([N:28]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH:29]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:30]=[O:31])[C:22]1[CH:27]=[CH:26][... | O=CC(Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1 | C=CCN1CCN(C(=O)OCc2ccccc2)CC1=O | 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 | null | 0.5 | Add to a solution of 4-benzyloxycarbonyl-1-allylpiperazin-2-one (1.1 g, 4.0 mmol) in dry THF (4 mL/mmol) at −78° C. under nitrogen lithium bis(trimethylsilyl)amide (1.OM solution in THF, 4.0 mL, 4.0 mmol) dropwise and stir 30 min. Add 2-(dibenzylamino)-3-phenylpropanal (732 mg, 2.2 mmol) in dry THF (2 mL/mmol) and stir... | C=CCN1CCN(C(=O)OCc2ccccc2)C(C(O)[C@H](Cc2ccccc2)N(Cc2ccccc2)Cc2ccccc2)C1=O | null | null | null |
1,606,021 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[C:17]3[C:18](=[CH:22][N:23]([CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[N:24]=3)[N:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][N:10]=1.C(N(CC)CC)C.[S:38](Cl)([CH3:41])(=[O:40])=[O:39]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:... | Cc1ccc(F)c(-c2cc(Nc3ccnc4cn(C5CCNCC5)nc34)ccn2)c1 | CS(=O)(=O)Cl | 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 solution of N-(2-(2-fluoro-5-methylphenyl)pyridin-4-yl)-2-(piperidin-4-yl)-2H-pyrazolo[4,3-b]pyridin-7-amine (49 mg, 0.122 mmol) in dichloromethane (3 mL) at 0° C. was added triethylamine (0.051 ml, 0.365 mmol) and mesyl chloride (10.41 μl, 0.134 mmol). The reaction was removed from the ice bath and briefly stirre... | Cc1ccc(F)c(-c2cc(Nc3ccnc4cn(C5CCN(S(C)(=O)=O)CC5)nc34)ccn2)c1 | null | 20.5 | null |
67,022 | ord_dataset-b5f1497361c94e5fa55257200189a6a4 | null | 1980-01-01T00:06:00 | true | [I-:1].Cl[C:3]1[CH:12]=[CH:11][C:10]2[N+:9]3[CH:13]=[C:14]4[CH:23]=[CH:22][C:21]5[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=5[N:15]4[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=1.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.CN1CCCC1=O>C(OCC)(=O)C>[I-:1].[N:24]1([C:3]2[CH:12]=[CH:11][C:10]3[N+:9]4[CH:13]=[C:14]5[CH:23]=[CH:22][C:21]6[CH:20... | Clc1ccc2c(ccc3n4c(ccc5ccccc54)c[n+]23)c1 | C1CCNC1 | null | [I-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1.0 g. of 3-chloroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide, 1.0 ml. of pyrrolidine and 5 ml. of N-methyl-2-pyrrolidinone is stirred and heated at reflux for 17 hours, cooled and diluted with 100 ml. of ethyl acetate. The precipitate of 3-(1-pyrrolidinyl)imidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is... | c1ccc2c(c1)ccc1c[n+]3c4ccc(N5CCCC5)cc4ccc3n12 | null | null | null |
293,751 | ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4 | null | 1994-01-01T00:07:00 | true | [F:1][C:2]1[CH:3]=[C:4]([C:19]2([O:25][CH3:26])[CH2:23][CH2:22][O:21][CH:20]2[CH3:24])[CH:5]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][CH3:17])=[CH:11][CH:10]=2)[CH:7]=1.Cl.[NH2:28][OH:29]>>[F:1][C:2]1[CH:3]=[C:4]([C:19]2([O:25][CH3:26])[CH2:23][CH2:22][O:21][CH:20]2[CH3:24])[CH:5]=[C:6]([S:8][C:9]2[CH:... | CCC(=O)c1ccc(Sc2cc(F)cc(C3(OC)CCOC3C)c2)cc1 | NO | 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 | Using an analogous procedure that described in Example 66, 4'-{5-fluoro-3-[(2RS,3SR)-3-methoxy-2-methyltetrahydrofuran-3-yl]phenylthio}propiophenone was reacted with hydroxylamine hydrochloride to give 4'-{5-fluoro-3-[(2RS,3SR)-3-methoxy-2-methyltetrahydrofuran-3-yl]phenylthio}propiophenone oxime in 15% yield, m.p. 113... | CCC(=NO)c1ccc(Sc2cc(F)cc(C3(OC)CCOC3C)c2)cc1 | null | 15 | null |
800,786 | ord_dataset-56a22bc0c3b14f87b9aa3f2fc6488ee7 | null | 2007-01-01T00:12:00 | true | O1CCCCC1[O:7][C@@H:8]1[CH2:12][O:11][CH:10]2[C@@H:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:28][CH:27]=4)=[CH:20][CH:19]=3)[CH2:14][O:15][CH:9]12.Cl>C(O)C>[OH:7][C@@H:8]1[CH2:12][O:11][CH:10]2[C@@H:13]([O:16][CH... | CCCCCCOc1ccc(C=Cc2ccc(CO[C@H]3COC4C3OC[C@H]4OC3CCCCO3)cc2)cc1 | 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 | The crude (E) 4-{3(R)-(tetrahydropyran-2-yloxy)-hexahydrofuro[3,2-b]furan-6(S)-yloxymethyl}-4′-hexyloxystilbene (19) was dissolved in 10 ml of ethanol and 0.5 ml of concentrated hydrochloric acid were added. Then the mixture was heated to reflux for 10 minutes. The product crystallized at room temperature. It was washe... | CCCCCCOc1ccc(C=Cc2ccc(CO[C@H]3COC4C3OC[C@H]4O)cc2)cc1 | null | 80 | null |
1,722,636 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][CH:9]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][CH:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:6][CH:5]=1 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(OC(F)(F)F)cc2)C1 | null | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | To a solution of tert-butyl 3-(4-(trifluoromethoxy)phenoxy)pyrrolidine-1-carboxylate (325 mg, 0.936 mmol) in CH2Cl2 (3.7 mL) was added TFA (360 μL, 4.68 mmol). The colorless solution was dried under reduced pressure and the crude oil obtained purified with a 5 g SCX-2 column washing first with MeOH, then with 2M NH3 in... | FC(F)(F)Oc1ccc(OC2CCNC2)cc1 | null | 82.2 | null |
1,515,904 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](I)[CH:15]=3)[C:10]([C:18]([OH:20])=[O:19])=[N:9]2)[C:5]([Cl:21])=[CH:4][N:3]=1.[CH3:22][C:23]1[O:27][N:26]=[C:25]([C@:28]([OH:32])([C:30]#[CH:31])[CH3:29])[N:24]=1>N1CCCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=... | Nc1ncc(Cl)c(-n2nc(C(=O)O)c3ccc(I)cc32)n1 | C#C[C@@](C)(O)c1noc(C)n1 | null | [Cu]I | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | 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 | 35 | null | To a solution of 1-(2-amino-5-chloropyrimidin-4-yl)-6-iodo-1H-indazole-3-carboxylic acid (400 mg, 0.96 mmol) in piperidine (4 mL) was introduced tetrakis(triphenylphosphine)palladium (0) (111 mg, 0.10 mmol), copper(I) iodide (18.3 mg, 0.10 mmol) and (2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol (292 mg, 1.92 mmol... | Cc1nc([C@](C)(O)C#Cc2ccc3c(C(=O)O)nn(-c4nc(N)ncc4Cl)c3c2)no1 | null | null | null |
961,784 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [CH:1]([CH:3]1[S:7][C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:17]([CH3:26])[S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])=[N:5][CH2:4]1)=O.[NH:27]1[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[O... | CN(c1cccc2cc(C3=NCC(C=O)S3)[nH]c12)S(=O)(=O)c1cccs1 | O=S1(=O)CCNCC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | O=C([O-])O | [Na+] | 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 | 0.17 | To a mixture of N-[2-(5-formyl-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (550 mg), thiomorpholine 1,1-dioxide (270 mg) and tetrahydrofuran (15 mL) was added sodium triacetoxyborohydride (420 mg) at room temperature, and the mixture was stirred for 10 min. Saturated aqueous sodium hydr... | CN(c1cccc2cc(C3=NCC(CN4CCS(=O)(=O)CC4)S3)[nH]c12)S(=O)(=O)c1cccs1 | null | 19.7 | null |
1,613,660 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | Br[C:2]1[CH:3]=[C:4]([N:22]([CH2:29][CH2:30][CH3:31])[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8].CC1(C)C(C)(C)OB([C:40]2[CH:52]=[CH:51][C:43]([CH2:44][N:45]3[CH2:50][CH2:49][O:48][CH2:47]... | CC1(C)OB(c2ccc(CN3CCOCC3)cc2)OC1(C)C | CCCN(c1cc(Br)cc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C)C1CCOCC1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | 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 | 100 | null | To a stirred solution of 5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-3-(propyl(tetrahydro-2H-pyran-4-yl)amino)benzamide (0.2 g, 0.412 mmol) and 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine (0.148 g, 0.488 mmol) in dioxane/water mixture (5 mL+1 mL), Na2CO3 (0.108 g, 1.0... | CCCN(c1cc(-c2ccc(CN3CCOCC3)cc2)cc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C)C1CCOCC1 | null | 82.7 | null |
1,203,707 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:27])[C:9]([C:15]2[CH:26]=[N:25][C:18]3[O:19][CH2:20][C:21](=[O:24])[N:22]([CH3:23])[C:17]=3[CH:16]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:28])[CH:3]=1.[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[C:36]([O:38][CH3:39])=[O:37]>>[CH3:39][O:38][C:36]([C:35]1[C... | COC(=O)c1ccc(B(O)O)cc1F | CC(c1ccc(Br)cc1Cl)C(O)(c1cnc2c(c1)N(C)C(=O)CO2)C(F)(F)F | 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 | In analogy to Example 17, step 2, 7-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyrido[2,3-b][1,4]oxazin-2-one was reacted with 3-fluoro-4-methoxycarbonylphenylboronic acid to give the title compound as a colorless solid. MS (m/e)=553.4 [M+H+]. | COC(=O)c1ccc(-c2ccc(C(C)C(O)(c3cnc4c(c3)N(C)C(=O)CO4)C(F)(F)F)c(Cl)c2)cc1F | null | null | null |
265,486 | ord_dataset-a2ae447c4340438c8c3a827109aeb425 | null | 1993-01-01T00:04:00 | true | [CH3:1]N.[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][C:23]([N+:24]([O-])=O)=[C:16]4[C:17]=3[C:12](=[CH:13][CH:14]=[CH:15]4)[C:11]2=[O:27])[CH2:6][CH2:5]1>C(O)(C)C>[CH3:1][NH:24][C:23]1[CH:22]=[CH:21][C:18]2[C:19](=[O:20])[N:10]([CH:7]3[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]3)[C:11]... | CN | CN1CCC(N2C(=O)c3cccc4c([N+](=O)[O-])ccc(c34)C2=O)CC1 | null | null | 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 | null | A mixture of 40% aqueous methylamine (2 mL) and 2,3-dihydro-2-(1-methylpiperidin-4-yl)-6-nitro-1H-benz[de]isoquinoline-1,3-dione (1.1 g; 3.14 mmol), prepared as in Example 3, in isopropanol (10 mL) was stirred at 65°-70° C. for six hours. Concentration of the solution followed by purification of the residue by column c... | CNc1ccc2c3c(cccc13)C(=O)N(C1CCN(C)CC1)C2=O | null | null | null |
538,717 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[N:12]1>O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:12]2[N:13]=[CH:14][CH:15]=[N:11]2)=[CH:3][CH:4]=1)([O-:10])=[O:9] | O=[N+]([O-])c1ccc(F)cc1 | c1c[nH]nn1 | null | null | null | 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 | null | null | 4-Fluoronitrobenzene (21 g) was reacted with 1H-1,2,3-triazole (12.4 g) in the same manner as in Reference Example 9. The resultant was cooled and poured into water. The precipitated crystals were collected by filtration and purified by silica gel chromatography (eluent: dichloromethane to dichloromethane/acetone=8/1).... | O=[N+]([O-])c1ccc(-n2nccn2)cc1 | null | 66.4 | null |
1,305,514 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([CH:8]([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1F.[CH:16]([N:29]1[CH2:32][CH:31]([C:33]#[N:34])[CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[CH:16]([N:29]1[CH2:32][C:31]([... | N#CC1CN(C(c2ccccc2)c2ccccc2)C1 | CCOC(OCC)c1ccc(F)c(Br)c1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [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 | 25 | 1 | To a solution of 2-bromo-4-(diethoxymethyl)-1-fluorobenzene (Preparation 15, 10.0 g, 36.0 mmol) in THF (125 mL) was added 1-benzhydrylazetidine-3-carbonitrile (13.4 g, 54.1 mmol) and KHMDS (10.8 g, 54.1 mmol). The reaction mixture is left stirring at room temperature for 1 hour. Next, the reaction mixture is concentrat... | CCOC(OCC)c1ccc(C2(C#N)CN(C(c3ccccc3)c3ccccc3)C2)c(Br)c1 | null | 75.3 | null |
954,932 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | CO[C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([S:15]([CH3:18])(=[O:17])=[O:16])[S:13][CH:14]=2)=[CH:6][CH:5]=1.[CH3:20][C@@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[CH2:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1>>[CH3:18][S:15]([C:12]1[S:13][CH:14]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([N:28]3[CH2:29][CH... | C[C@@H]1CCCN1C[C@@H]1CCCN1 | COC(=O)c1ccc(-c2csc(S(C)(=O)=O)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 title compound is prepared in a manner substantially analogous to Procedure N and Procedure P starting from 4-(2-Methanesulfonyl-thiazol-4-yl)-benzoic acid methyl ester and 2-(R)-Methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine. MS (ES+) 434.12. | C[C@@H]1CCCN1C[C@@H]1CCCN1C(=O)c1ccc(-c2csc(S(C)(=O)=O)n2)cc1 | null | null | null |
1,467,763 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | C[O:2][C:3](=[O:15])[C:4]1[C:5](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([Cl:11])[CH:10]=1)[NH2:6].[Li+].[OH-].Cl>C1COCC1.O>[Cl:11][C:9]1[CH:10]=[C:4]([C:3]([OH:15])=[O:2])[C:5]([NH2:6])=[CH:7][C:8]=1[N+:12]([O-:14])=[O:13] | COC(=O)c1cc(Cl)c([N+](=O)[O-])cc1N | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of 5-chloro-4-nitroanthranilic acid methyl ester (10.0 g, 43 mmol) in THF (120 mL) was added LiOH (2.7 g, 65 mmol) dissolved in water (40 mL). The reaction mixture was stirred at room temperature for 18 h and acidified to pH 4 with 1 N HCl. The aqueous layer was extracted with EtOAc (2×150 mL); the combin... | Nc1cc([N+](=O)[O-])c(Cl)cc1C(=O)O | null | 93.4 | null |
1,604,899 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:13][CH3:14])[CH:11]=2)[CH:6]=[C:5]1[C:15](=O)[CH:16]([CH3:18])[CH3:17].CCN(CC)CC.[BH4-].[Na+]>CO>[CH:16]([CH:15]1[C:5]2=[CH:6][C:7]3[CH:8]=[CH:9][C:10]([S:13][CH3:14])=[CH:11][C:12]=3[N:4]2[CH2:3][CH2:2][NH:1]1)([CH3:18])[CH3:17] | CSc1ccc2cc(C(=O)C(C)C)n(CCN)c2c1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 60 | 1 | To a solution of 1-(1-(2-aminoethyl)-6-(methylthio)-1H-indol-2-yl)-2-methylpropan-1-one (200 mg, 0.724 mmol) in MeOH (5 mL) was added Et3N (219.3 mg, 2.172 mmol). The reaction mixture was stirred at 60° C. for 1 h. Then NaBH4 (82.53 mg, 2.172 mmol) was added to the formed mixture. The mixture was stirred at 60° C. for ... | CSc1ccc2cc3n(c2c1)CCNC3C(C)C | null | 42.4 | null |
887,669 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=2[F:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:28][OH:29]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:... | NO | CC(C)(C)OC(=O)N1CCC(C(=O)c2cc(C(F)(F)F)ccc2F)CC1 | null | Cl | 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 | 25 | 14 | A solution of 4-(2-fluoro-5-trifluromethyl-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester (5 g, 0.013M) in pyridine (25 mL) was treated with hydroxylamine hydrochloride (1.11 g, 0.015 M -1.2 eq). The reaction was stirred under N2 at room temperature for 14 hours and then poured onto ice water (250 mL). The mixt... | CC(C)(C)OC(=O)N1CCC(C(=NO)c2cc(C(F)(F)F)ccc2F)CC1 | null | null | null |
1,584,575 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | Br[C:2]1[C:18]([F:19])=[CH:17][C:5]2[O:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([C:14]([NH2:16])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1.[C:20]([C:22]1([OH:30])[CH2:27][CH2:26][CH2:25][N:24]([CH3:28])[C:23]1=[O:29])#[CH:21]>>[F:19][C:18]1[C:2]([C:21]#[C:20][C:22]2([OH:30])[CH2:27][CH2:26][CH2:25][N:24]([CH3:28])[C:23]2=[O:29])... | NC(=O)c1nc2c(s1)CCOc1cc(F)c(Br)cc1-2 | C#CC1(O)CCCN(C)C1=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 | Similar to as described in General Procedure G, 9-bromo-8-fluoro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide was reacted with 3-ethynyl-3-hydroxy-1-methylpiperidin-2-one (US2012/214762A1) to give the titled compound as a white solid (20 mg, 16%). | CN1CCCC(O)(C#Cc2cc3c(cc2F)OCCc2sc(C(N)=O)nc2-3)C1=O | null | 16 | null |
1,572,857 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([S:20]([NH:23]CCP(=O)(O)O)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.N[CH2:31][P:32](=[O:39])([O:36]CC)[O:33]CC>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2... | CCOP(=O)(CN)OCC | CN1Cc2c(Cl)cc(Cl)cc2C(c2cccc(S(=O)(=O)NCCP(=O)(O)O)c2)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 5 was prepared in an analogous manner to that of Compound 1 using diethyl aminomethylphosphonate (Intermediate 5.3) as the amine. 1H-NMR (300 MHz, CD3OD, ppm): 7.89 (d, J=7.8 Hz, 1H), 7.74 (s, 1H), 7.63˜7.66 (m, 1H), 7.57˜7.61 (m, 2H), 6.97 (s, 1H), 4.80˜4.89 (m, 1H), 4.55˜4.67 (m, 2H), 3.83˜3.89 (m, 1H), 3.55... | CN1Cc2c(Cl)cc(Cl)cc2C(c2cccc(S(=O)(=O)NCP(=O)(O)O)c2)C1 | null | null | null |
675,341 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | I[C:2]1[N:3]=[CH:4][N:5]2[CH:9]=[CH:8][S:7][C:6]=12.C[Mg]Br.C1COCC1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=[O:25])[CH:19]=1.O>C1COCC1>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([OH:25])[C:2]2[N:3]=[CH:4][N:5]3[CH:9]=[CH:8][S:7][C:6]=23)[CH:19]=1 | Ic1ncn2ccsc12 | O=Cc1cccnc1 | null | C[Mg]Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | 0.33 | A solution of 2.50 g of 7-iodoimidazo[5,1-b]thiazole in 50 ml of dry THF was cooled in ice, and 11.3 ml of a 0.93 M methylmagnesium bromide/THF solution was added to the cooled solution under an argon atmosphere. The mixture was stirred at that temperature for 20 min. Pyridine-3-aldehyde (1.04 ml) was then added theret... | OC(c1cccnc1)c1ncn2ccsc12 | null | null | null |
438,131 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[C:21]2[O:22]CC(C)(C)N=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CI.[N+](C)([O-])=[O:31]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[C:21]([OH:31])=[O:22])[... | COc1ccc(-c2cc(OC)c(OC)cc2C2=NC(C)(C)CO2)cc1OC | C[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | null | null | null | null | null | null | null | null | null | null | null | 24 | 2-[2-(3,4-Dimethoxyphenyl)-4,5-dimethoxyphenyl]-4,4-dimethyl-2-oxazoline (10 g) was dissolved in nitromethane (100 ml), to which was added methyl iodide (10 ml), and the mixture was allowed to stand at room temperature for 24 hours. It was concentrated by an evaporator, and methanol (150 ml) and a 20% aqueous sodium hy... | COc1ccc(-c2cc(OC)c(OC)cc2C(=O)O)cc1OC | null | null | null |
432,009 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:22]=[CH:21][C:13]3[O:14][C:15]([CH3:20])([CH3:19])[C:16]([CH3:18])=[CH:17][C:12]=3[CH:11]=2)=[CH:5][CH:4]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C.ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[CH:22]=[CH:21][C:13]3[O:14][C:15]([CH3:19])([CH3:20])[C:16]([CH3:18])=[CH:17][C:12]=3... | COc1ccc(Sc2ccc3c(c2)C=C(C)C(C)(C)O3)cc1 | null | null | [I-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1cc(C)nc(C)c1 | ClCCl | null | null | null | null | null | null | null | null | null | null | 72 | 6-(4-Methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (7.816 g) (see Preparation 5) was dissolved in dry 2,4,6-collidine (30 ml), anhydrous lithium iodide (10.04 g) was added and the mixture was heated under reflux under.a nitrogen atmosphere for 48 hours. A further portion of lithium iodide (9.06. g) was then added... | CC1=Cc2cc(Sc3ccc(O)cc3)ccc2OC1(C)C | null | 77.7 | null |
1,027,603 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]([F:10])([F:11])[CH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1 | OC1CCC(C(F)(F)F)CC1 | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | 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 | 2 | To a solution of 4-Trifluoromethylcyclohexanol (4.5 g, 26.7 mmol) in DCM (100 ml) was added Dess-Martin periodinane (13.6 g, 32 mmol), and stirred at rt for 2 h. After the reaction finished, the reaction mixture was concentrated in vacuo, sodium thiosulfate aqueous solution and diethylether were added and stirred at rt... | O=C1CCC(C(F)(F)F)CC1 | null | 94.7 | null |
1,512,006 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[N:15]([C:16]3[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=3)[N:14]=[C:13]([C:23](OCC)=[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:7]=[CH:6][C:5]([S:8]([C:11]2[N:15]([C:16]3[C:17]([F:22])=[N:18][CH:19]=[CH:2... | CCOC(=O)c1cc(S(=O)(=O)c2ccc(F)cc2)n(-c2cccnc2F)n1 | 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 | C1CCOC1 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of ethyl 5-[(4-fluorophenyl)sulfonyl]-1-(2-fluoropyridin-3-yl)-1H-pyrazole-3-carboxylate (170 mg) in tetrahydrofuran (2.5 mL) was cooled to −78° C., and a 1.5 mol/L solution (1.2 mL) of diisobutylaluminum hydride in toluene was added dropwise. The reaction mixture was stirred at room temperature for 1 hr, tr... | O=S(=O)(c1ccc(F)cc1)c1cc(CO)nn1-c1cccnc1F | null | 88.9 | null |
268,202 | ord_dataset-134cf2fa32ab464880d75db06c38f35a | null | 1993-01-01T00:05:00 | true | [F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][CH2:19][NH2:20])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:24][N:25]([CH2:27][C:28]1[O:44][C:31]([CH2:32][S:33][CH2:34][CH2:35][NH:36][CH:37](SC)[CH2:38][N+:39]([O-:41])=[O:40])=[CH:30][CH:29]=1)[CH3:26]>... | CSC(C[N+](=O)[O-])NCCSCc1ccc(CN(C)C)o1 | CN(CCCN)CCN(Cc1ccc(F)cc1)c1ccccn1 | 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 | Preparation is effected analogously to Example 22, using 0.54 g (1.7 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine and the equimolar amount of 1-[2-[[5-[(dimethylamino)methyl]furfuryl]thio]ethyl]amino-1-methylthio-2-nitroethane as starting materials. Working up by chromatograph... | CN(C)Cc1ccc(CSCCNC(=C[N+](=O)[O-])NCCCN(C)CCN(Cc2ccc(F)cc2)c2ccccn2)o1 | null | null | null |
60,567 | ord_dataset-912d62c1690b4ebfbe998c0c9baf88a8 | null | 1979-01-01T00:12:00 | true | [OH:1][CH2:2][C:3]([O:5][C@:6]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:7](=[O:9])[CH3:8])=[O:4].[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([O:1][CH2:2][C:3]([O:5][C@:6]1([C@:26]2([CH... | CC(=O)OC(C)=O | CC(=O)[C@@]1(OC(=O)CO)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | 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 | The above alcohol is acetylated with acetic anhydride in pyridine to give 17α-acetoxyacetoxypregn-4-ene-3,20-dione, which shows the following significant NMR signals: δ(ppm) 0.69 (s, 3H, H-18), 1.19 (s, 3H, H-19), 2.07 and 2.17 (singlets, 3H each, 2-COCH3), ##STR28## 5.76 (broad s, 1H, H-4). | CC(=O)OCC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C | null | null | null |
1,522,576 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.[H-].[Na+].[Li]C(C)(C)C.[CH3:19][C:20]1([CH3:31])[C:24]([CH3:26])([CH3:25])[O:23][B:22](OC(C)C)[O:21]1>O1CCCC1>[CH3:11][C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([B:22]1[O:23][C:24]([CH3:26])([CH3:25])[C:20]([CH3:31])([CH3:19])[O:21]1)=[CH:10]... | Cc1cc2cc(Br)ccc2[nH]1 | CC(C)OB1OC(C)(C)C(C)(C)O1 | null | [H-] | [Li]C(C)(C)C | [Na+] | 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 | -40 | 0.5 | To a solution of 5-bromo-2-methyl-1H-indole (3.0 g, 14.35 mmol) in dry tetrahydrofuran (20 ml) was added sodium hydride (900 mg, 22.5 mmol) with ice-cooling. After stifling for about 30 min, a solution of t-BuLi (27.5 ml, 1.3 M solution in hexane) was added dropwise with stifling at −78° C. under an inert atmosphere of... | Cc1cc2cc(B3OC(C)(C)C(C)(C)O3)ccc2[nH]1 | null | 37.9 | null |
26,681 | ord_dataset-2ada3fda46fc44719ba0c8001f53c1b3 | null | 1977-01-01T00:06:00 | true | [ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:26])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18]CC2C=CC=CC=2)[CH:13]=1.C(O)(C)C>[C].[Pd].O>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][CH2:8][NH:9][CH2:10][CH:11](... | COc1ccc(CCNCC(O)c2cccc(OCc3ccccc3)c2)cc1OC | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | 2 g of α-(3,4-dimethoxyphenethylaminomethyl)-3-benzyloxybenzylalcohol hydrochloride, 0.5 g of 10 % palladium-carbon, 100 ml of isopropanol and 15 ml of water are treated in the same manner as described in Example 1-(c). 1.45 g of α-(3,4dimethoxyphenethylaminomethyl)-3-hydroxybenzylalcohol hydrochloride are obtained. M.... | COc1ccc(CCNCC(O)c2cccc(O)c2)cc1OC | null | 91 | null |
277,949 | ord_dataset-ad17798fcea64e26ba91604fca520090 | null | 1993-01-01T00:10:00 | true | [H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[C:8]([F:10])[CH:9]=1.I[CH2:18][CH:19]([CH3:24])[O:20][CH2:21][CH2:22]I>C1COCC1>[CH2:15]([O:14][C:12]([C:11]1([C:6]2[CH:5]=[C:4]([F:3])[CH:9]=[C:8]([F:10])[CH:7]=2)[CH2:22][CH2:21][O:20][CH:19]([CH3:24])[CH2:18]1)=[O:13])[CH3:16] | CCOC(=O)Cc1cc(F)cc(F)c1 | CC(CI)OCCI | null | [H-] | [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 | 25 | 1 | Sodium hydride (60% w/w dispersion in mineral oil, 9.17 g) was added portionwise to a solution of ethyl 3,5-difluorophenylacetate (17 S) in THF (400 ml) and the mixture was stirred at ambient temperature for 1 hour. A solution of 1,5-diiodo-2-methyl-3-oxapentane (30.3 g) in THF (20 ml) was added dropwise and the mixtur... | CCOC(=O)C1(c2cc(F)cc(F)c2)CCOC(C)C1 | null | null | null |
1,712,161 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH:20]=[C:13]2[CH:14]=[N+:15]([O-])[CH:16]=[C:17]([F:18])[C:12]2=[N:11]1.P(Br)(Br)([Br:23])=O>ClCCCl.C(Cl)Cl>[Br:23][C:14]1[C:13]2=[CH:20][N:10]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=3[Cl:9])[N:11]=[C:12]2[C:17]([F:18])=[CH:16][N:15]=1 | O=P(Br)(Br)Br | [O-][n+]1cc(F)c2nn(-c3c(Cl)cc(F)cc3Cl)cc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | ClCCCl | null | null | null | null | null | null | null | null | null | 0 | 1 | To a cooled (0° C.) suspension of 2-(2,6-dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine-5-oxide (2.95 g, 9.3 mmol) in DCE (50 mL) was added phosphorus oxybromide (8.0 g, 28 mmol). The reaction mixture was stirred at 0° C. for 1 hour, warmed to room temperature, and stirred for a further 3 hours. The react... | Fc1cc(Cl)c(-n2cc3c(Br)ncc(F)c3n2)c(Cl)c1 | null | 28.4 | null |
170,320 | ord_dataset-37d3220f708c49ad839bab296b722248 | null | 1988-01-01T00:03:00 | true | [CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][C:7](=[O:11])[CH2:6][C:5]=2[CH:4]=[N:3]1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[CH3:14][N:15]([CH:17]=[C:6]1[C:7](=[O:11])[CH2:8][CH2:9][C:10]2[N:2]([CH3:1])[N:3]=[CH:4][C:5]1=2)[CH3:16] | COC(OC)N(C)C | Cn1ncc2c1CCC(=O)C2 | 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 above procedure was repeated using 1,4,6,7-tetrahydro-1-methyl-5H-indazol-5-one and N,N-dimethylformamide dimethyl acetal. The crude product was flash chromatographed (5% methanol in dichloromethane) on silica gel to give a thick amber oil which was triturated with etherhexane to give 4-(dimethylaminomethylene) 1,4... | CN(C)C=C1C(=O)CCc2c1cnn2C | null | null | null |
1,080,362 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | FC(F)(F)C(O)=O.[C:8]([NH:16][C:17]1[CH:29]=[C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([N+:37]([O-:39])=[O:38])[CH:32]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:8]([NH:16][C:17]1[CH:29]=[C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([N+:37... | CC(C)(C)OC(=O)c1ccc(Oc2cccc([N+](=O)[O-])c2)cc1NC(=O)c1ccccc1 | null | 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 | 25 | 3 | 5.0 mL of trifluoroacetic acid was added to the obtained tert-butyl 2-(benzamido)-4-(3-nitrophenoxy)benzoate and stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure and diisopropyl ether was added to the obtained residue and a solid substance was separated by filtration to obtain ... | O=C(Nc1cc(Oc2cccc([N+](=O)[O-])c2)ccc1C(=O)O)c1ccccc1 | null | null | null |
1,215,654 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[NH2:16][CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[C:18]([OH:20])=[O:19]>CS(C)=O>[Br:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH:17]([NH:16][C:2]2[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9... | O=C(O)c1cc2cc(Cl)ccc2nc1Cl | NC(Cc1ccc(Br)cc1)C(=O)O | 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 | null | In close analogy to the procedure described in Example 1, 2,6-dichloroquinoline-3-carboxylic acid is reacted with 2-amino-3-(4-bromo-phenyl)-propionic acid in DMSO to provide the title compound in good yield. | O=C(O)c1cc2cc(Cl)ccc2nc1NC(Cc1ccc(Br)cc1)C(=O)O | null | null | null |
514,875 | ord_dataset-41760195182e4bb4bc779bd722456071 | null | 2001-01-01T00:08:00 | true | [C:1]([Cl:4])(Cl)=[O:2].[CH2:5]([NH:8][CH:9]1[CH2:13][CH2:12][O:11][CH2:10]1)[CH2:6][CH3:7].C(N(CC)CC)C>>[CH2:5]([N:8]([CH:9]1[CH2:13][CH2:12][O:11][CH2:10]1)[C:1]([Cl:4])=[O:2])[CH2:6][CH3:7] | CCCNC1CCOC1 | O=C(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | 94 g (0.95 mol) of phosgene, 41 g (0.32 mol) of N-propyl-N-(tetrahydrofuran-3-yl)amine and 32 g (0.32 mol) of triethylamine were reacted by the method of the process described in Intermediate 1.2. Yield 54 g. 1H NMR (270 MHz, in CDCl3): δ=0.92 (t, 3H), 1.70 (sext., 2H), 2.02 (s, 1H), 2.30 (s, 1H), 3.20-3.40 (m, 2H), 3.... | CCCN(C(=O)Cl)C1CCOC1 | null | null | null |
1,160,037 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[S:9]([C@H:12]1[CH2:16][N:15]([C:17]2[N:21]([CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[N:20]=[C:19]([CH3:28])[CH:18]=2)[C@H:14]([C:29]([NH:31][C:32]2([C:35]#[N:36])[CH2:34][CH2:33]2)=[O:30])[CH2:13]1)(=[O:11])=[O:10].[NH:37]1[CH:41]=[CH:40][CH:39]=[N:38]1>>[C:35]([C:... | c1cn[nH]c1 | Cc1cc(N2C[C@H](S(=O)(=O)c3ccc(F)cc3Cl)C[C@H]2C(=O)NC2(C#N)CC2)n(C2CCOCC2)n1 | 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 | In analogy to the procedure described in example 416, (2S,4R)-4-(2-chloro-4-fluorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl)pyrrolidine-2-carboxamide (example 464d) was reacted with pyrazole (CAS Reg. No. 288-11-9) to give the title compound as colorless oil. MS (ES... | Cc1cc(N2CC(S(=O)(=O)c3ccc(-n4cccn4)cc3Cl)CC2C(=O)NC2(C#N)CC2)n(C2CCOCC2)n1 | null | null | null |
1,658,235 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | Cl[C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1[Cl:8].[F:13][CH:14]([F:17])[CH2:15][NH2:16].CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:8][C:7]1[N:6]=[C:5]2[CH:9]=[N:10][CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[NH:16][CH2:15][CH:14]([F:17])[F:13] | NCC(F)F | Clc1nc2ccncc2nc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1COCCO1 | null | null | null | null | null | null | null | null | null | 70 | 1 | A solution of 2,3-dichloropyrido[3,4-b]pyrazine (50 mg, 0.250 mmol) in dioxane (250 μL) was treated with 2,2-difluoroethanamine (21.0 μL, 0.275 mmol) and DIPEA (131 μL, 0.750 mmol). The resulting reaction mixture was stirred at 70° C. for 1 h then purified by flash silica gel chromatography using a gradient of 0% to 60... | FC(F)CNc1nc2ccncc2nc1Cl | null | 85 | null |
1,666,222 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([C@@H:18]3[CH2:20][C@H:19]3[CH:21]=O)[CH:9]=2)[N:3]=1.[CH3:23][NH:24][C:25]1[C:26]([NH2:31])=[CH:27][CH:28]=[CH:29][CH:30]=1.CC(O)=O>C(O)C.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C... | CNc1ccccc1N | Cc1nc(C)n(-c2cc([C@@H]3C[C@H]3C=O)nc(C(F)(F)F)n2)n1 | null | [Cu+2] | O=S(=O)([O-])[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CCO | null | null | null | null | null | null | null | null | null | 25 | 4 | To the mixture of trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropanecarbaldehyde (16-6, 280 mg, 0.899 mmol, 1.0 eq.) and N1-methylbenzene-1,2-diamine (0.11 mL, 0.989 mmol, 1.1 eq.) in anhydrous ethanol (5.0 mL) at room temperature was added glacial AcOH (0.062 mL, 1.08 mmol, ... | Cc1nc(C)n(-c2cc([C@@H]3C[C@H]3c3nc4ccccc4n3C)nc(C(F)(F)F)n2)n1 | null | null | null |
179,582 | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | null | 1988-01-01T00:11:00 | true | [N+:1]([O-:4])(O)=[O:2].C(=O)=O.[O:8]=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]1[CH2:19][C:20]([OH:22])=[O:21]>CO>[N+:1]([C:16]1[CH:17]=[C:18]2[C:13]([CH2:12][CH2:11][CH:10]([CH2:19][C:20]([OH:22])=[O:21])[C:9]2=[O:8])=[CH:14][CH:15]=1)([O-:4])=[O:2] | O=[N+]([O-])O | O=C(O)CC1CCc2ccccc2C1=O | null | O=C=O | null | 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 | 0.67 | To nitric acid (density=1.50) cooled with dry ice and methanol is added 1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetic acid at -10 to -15° C. The resulting mixture is stirred below 0° C. for 40 minutes and poured into ice. The precipitated crystals are collected by filtration to give 7-nitro-1,2,3,4-tetrahydro-1-oxo-2-na... | O=C(O)CC1CCc2ccc([N+](=O)[O-])cc2C1=O | null | null | null |
1,424,336 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:23])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][NH:28][CH3:29]>>[CH3:24][N:25]([CH3:30])[CH2:26][CH2:27][N:28]([CH3:29])[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](... | CN(C)CCNc1cccc2c1C(=O)c1cccc(Cl)c1C2=O | CNCCN(C)C | 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 | This procedure was carried out as described previously in Example 19, using Compound 17 (500 mg, 1.52 mmol) and N,N,N′-trimethylethylenediamine (988 μL, 7.6 mmol). The dye was obtained as a red solid (260 mg) after Biotage purification using a gradient of methanol in chloroform. Abs (max, PBS pH 7.4)=530 nm; Em=646 nm.... | CN(C)CCNc1cccc2c1C(=O)c1cccc(N(C)CCN(C)C)c1C2=O | null | 43.4 | null |
1,043,431 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[F:18][C:19]1[CH:20]=[C:21]([C:25]#[C:26][C:27]2[CH:28]=[N:29][CH:30]=[C:31]([CH:38]=2)[C:32](N(OC)C)=[O:33])[CH:22]=[CH:23][CH:24]=1>>[F:18][C:19]1[CH:20]=[C:21]([C:25]#[C:26][C:27]2[CH:38]=[C:31]([CH:32]=[O:33])[CH:30]=[N:29][CH:28]=2)[CH:22]=[CH:23][CH:24]=1 | CON(C)C(=O)c1cncc(C#Cc2cccc(F)c2)c1 | 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 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | Prepare essentially as described in EXAMPLE 5 using a 1 M solution of diisobutylaluminum hydride in toluene (1.2 mL, 1.20 mmol), 5-(3-fluorophenylethynyl)-N-methoxy-N-methylnicotinamide, (prepared as described in PREPARATION 18), (170 mg, 0.60 mmol) to give the title compound (86 mg, 64%). | O=Cc1cncc(C#Cc2cccc(F)c2)c1 | null | 63.6 | null |
1,091,580 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([Mg]Cl)[C:11]([CH3:14])([CH3:13])[CH3:12]>C1COCC1.[NH4+].[Cl-]>[CH3:10][C:11]([CH3:14])([CH3:13])[CH2:12][CH:6]([C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=1)[OH:7] | CC(C)(C)C[Mg]Cl | Cc1ccc(C=O)cc1 | null | [Cl-] | [NH4+] | 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 | 0 | 1 | To a stirred solution of 4-methylbenzaldehyde (1.51 g, 12.6 mmol) in THF (30 mL) at 0° C., add neopentyl magnesium chloride (33.0 mL, 16.34 mmol, 0.5-1M in ether) and continue stirring at 0° C. for 1 h. Dilute with saturated aqueous NH4Cl, extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in va... | Cc1ccc(C(O)CC(C)(C)C)cc1 | null | 88.7 | null |
995,806 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [NH2:1][CH2:2][C@H:3]1[O:8][C@@:7]2([C:16]3[C:11](=[CH:12][C:13]([Cl:26])=[C:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=4)[CH:15]=3)[CH2:10][O:9]2)[C@H:6]([OH:27])[C@@H:5]([OH:28])[C@@H:4]1[OH:29].N1C=CC=CC=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:26][C:13]1[CH:12]=[C... | CC(=O)OC(C)=O | CCc1ccc(Cc2cc3c(cc2Cl)CO[C@]32O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)cc1 | null | CN(C)c1ccncc1 | 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 | 2 | To a stirred solution of (1S,3′R,4′S,5′S,6′R)-6′-(aminomethyl)-5-chloro-6-(4-ethylbenzyl)-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-3′,4′,5′-triol (20 mg, 0.047 mmol) and 0.04 mL of pyridine in 1 mL of dichloromethane, was added acetic anhydride (45 μL, 0.048 mmol) and 3 mg of 4-dimethylaminopyridine. A... | CCc1ccc(Cc2cc3c(cc2Cl)CO[C@]32O[C@H](CNC(C)=O)[C@@H](O)[C@H](O)[C@H]2O)cc1 | null | 23 | null |
908,420 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]1)[CH:8]=[CH:7]2)([O-])=O>ClCCl.CO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]1)[CH:8]=[CH:7]2 | O=[N+]([O-])c1ccc2nc(C3CCCCN3)ccc2c1 | null | null | null | null | 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 | null | null | Prepared analogously to Example 3.1.b. from 6-nitro-2-piperidin-2-yl-quinoline. Yield: 0.79 g (59.6% of theory); C14H17N3 (M=227.31); calc.: molecular ion peak (M+H)+: 228; found: molecular ion peak (M+H)+: 228; Rf value: 0.37 (silica gel, dichloromethane/methanol (19:1)). | Nc1ccc2nc(C3CCCCN3)ccc2c1 | null | null | null |
301,266 | ord_dataset-9ad0840101374618a7d5c4e4521c82d1 | null | 1994-01-01T00:12:00 | true | [F:1][C:2]1[C:3](Cl)=[N:4][C:5]([NH2:9])=[N:6][C:7]=1[Cl:8].[OH-].[NH4+:12]>C(O)C>[F:1][C:2]1[C:3]([NH2:12])=[N:4][C:5]([NH2:9])=[N:6][C:7]=1[Cl:8] | [NH4+] | Nc1nc(Cl)c(F)c(Cl)n1 | null | [OH-] | 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 | 100 | null | 5-Fluoro-4,6-dichloro-2-pyrimidineamine (4) (204 mg, 1 mmol) and ammonium hydroxide (15 ml) were charged to a sealed tube and ethanol (1.5 ml) added. The tube was heated at 100° C. for 24 hours. The solution was concentrated. The residue was absorbed on silica gel and chromatographed (elution with ethyl acetate), yield... | Nc1nc(N)c(F)c(Cl)n1 | null | 65 | null |
159,357 | ord_dataset-41c90677d90b4fa5836ab66e2f5b4f51 | null | 1987-01-01T00:06:00 | true | [C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:10](=[O:27])[CH2:11][NH:12][C@H:13]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:28][CH:29]([CH3... | CC(C)C[C@H](NC(=O)OC(C)(C)C)C(=O)CN[C@@H](CC(C)C)C(=O)OCC[Si](C)(C)C | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | 0.08 | To a solution of 5.0 g (10.9 mmol) of N-[(3S)-3-[[(t-butyloxy)carbonyl]amino]-2-oxo-5-methylhexyl]-L-leucine, 2-(trimethylsilyl)ethyl ester in a mixture of 150 ml of tetrahydrofuran and 50 ml of water cooled in an ice-water bath was added 2.1 g (54.5 mmol) of sodium borohydride. After 5 minutes, the reaction was poured... | CC(C)C[C@H](NCC(O)[C@H](CC(C)C)NC(=O)OC(C)(C)C)C(=O)OCC[Si](C)(C)C | null | 69.7 | null |
619,596 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([OH:17])=O)[CH3:14])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:18][CH:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:26][CH:27]=2)[CH2:22][NH:21][C:20]1=[O:35]>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([... | C[C@H](NC(=O)Cc1cc(F)cc(F)c1)C(=O)O | NC1C(=O)NCc2cc(-c3ccccc3)ccc21 | 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 D above using N-(3,5-difluorophenylacetyl)-L-alanine (Example B) and 4-amino-7-phenyl-1,2,3,4-tetrahydroisoquinoline-3-one (Example 5-H), the title compound was prepared as a solid having a melting point >240° C. (dec.). | C[C@H](NC(=O)Cc1cc(F)cc(F)c1)C(=O)NC1C(=O)NCc2cc(-c3ccccc3)ccc21 | null | null | null |
1,255,443 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [NH2:1][C:2]1([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6][C:5]([F:8])=[CH:4][CH2:3]1.[H][H]>CO.C(OCC)(=O)C.[C].[Pd]>[NH2:1][C:2]1([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6][CH:5]([F:8])[CH2:4][CH2:3]1 | COC(=O)C1(N)CC=C(F)CC1 | [H][H] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | null | null | Methyl 1-amino-4-fluoro-3-cyclohexenecarboxylate (52 mg) was dissolved in the mixed solvents of methanol (2 mL) and ethyl acetate (2 mL), and 10% palladium-carbon (35 mg) was added and hydrogen gas was introduced for 14 hours. The insoluble matter was filtered and the solvent was removed by distillation under reduced p... | COC(=O)C1(N)CCC(F)CC1 | null | null | null |
1,235,295 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[C:33]([OH:38])[CH:34]=[CH:35][CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:39])[CH2:22][CH2:21]3)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]... | CCOC(=O)CBr | CC(C)(C)OC(=O)N(Cc1ccc2c(c1)OCCO2)C1CCN(CCn2c(=O)ccc3c(O)cccc32)CC1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | To 3 mL of an N,N-dimethylformamide solution containing 166 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-hydroxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 65 mg of potassium carbonate and 43 μL of ethyl bromoacetate were added, and stirred at room temperature for 2 hours. After water w... | CCOC(=O)COc1cccc2c1ccc(=O)n2CCN1CCC(N(Cc2ccc3c(c2)OCCO3)C(=O)OC(C)(C)C)CC1 | null | null | null |
1,666,673 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:29][CH2:28][C:11]3([CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:30][C@H:31]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH3:44])=[CH:38][C:37]=2[C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([S:51]([CH3:54])(=[O:53])=... | CCCc1ccc([C@@H](Oc2cc(N3CCC4(CC3)C[C@@H](C(=O)OCC)N(C(=O)OC(C)(C)C)C4)nc(N)n2)C(F)(F)F)c(-c2cccc(S(C)(=O)=O)c2)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 | 25 | 2 | To a solution of (S)-2-tert-butyl 3-ethyl 8-(2-amino-6-((R)-2,2,2-trifluoro-1-(3′-(methylsulfonyl)-5-propyl-[1,1′-biphenyl]-2-yl)ethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate in CH2Cl2 (4 mL) was added TFA (2.0 mL) dropwise at 0° C. The reaction mixture was stirred at RT for 2 h, then concentrated ... | CCCc1ccc([C@@H](Oc2cc(N3CCC4(CC3)CN[C@H](C(=O)OCC)C4)nc(N)n2)C(F)(F)F)c(-c2cccc(S(C)(=O)=O)c2)c1 | null | null | null |
1,024,362 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C@@H:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]1.[ClH:27]>O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C@@H:7]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C@@H:8]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]1.[... | COCCCO[C@@H](c1ccccc1)[C@@H]1CCCN(C(=O)OC(C)(C)C)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 | 0.5 | (R)-tert-Butyl 3-((R)-(3-methoxypropoxy)(phenyl)methyl)piperidine-1-carboxylate (27 mg, 0.074 mmol) was mixed with 4M HCl in 1,4-dioxane (3 mL) and stirred for 30 min at rt. LC-MS showed complete removal of the Boc protecting group. The mixture was concentrated to afford (R)-3-((R)-(3-methoxypropoxy)(phenyl)methyl)pipe... | COCCCO[C@@H](c1ccccc1)[C@@H]1CCCNC1 | null | null | null |
1,120,898 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [Cl:1][C:2]1[C:3]([N+:26]([O-])=O)=[CH:4][C:5]([CH3:25])=[C:6]([CH:24]=1)[O:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.C([O-])=O.[NH4+].C1(C)C=CC=CC=1>[Fe].O>[NH2:26][C:3]1[C:2]([Cl:1])=[CH:24][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[C... | Cc1cc([N+](=O)[O-])c(Cl)cc1OCCCN1CCN(C(=O)OC(C)(C)C)CC1 | null | null | [Fe] | O=C[O-] | [NH4+] | 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 | null | null | A flask was charged with tert-butyl 4-(3-(5-chloro-2-methyl-4-nitrophenoxy)propyl)-piperazine-1-carboxylate (1.2 g, 2.9 mmol), ammonium formate (0.84 g, 13 mmol), and iron powder (0.74 g, 13 mmol). Toluene (20 mL) and water (20 mL) were added to the flask and the mixture was heated to reflux for 6 hours, after which ti... | Cc1cc(N)c(Cl)cc1OCCCN1CCN(C(=O)OC(C)(C)C)CC1 | null | 88.9 | null |
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