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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,676,700 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | N1C=CN=C1CN1C(=O)C[O:10][C:9]2N=C(C3C=CC(C4(N)CCC4)=CC=3)C(C3C=CC=CC=3)=CC1=2.C(OC(=O)[NH:41][C:42]1([C:46]2[CH:51]=[CH:50][C:49]([C:52]3[C:53]([C:69]4[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=4)=[CH:54][C:55]4[N:60]([CH2:61][C:62]5([CH3:66])C[O:64][CH2:63]5)[C:59](=[O:67])[CH2:58][O:57][C:56]=4[N:68]=3)=[CH:48][CH:47]=2)[... | CC1(CN2C(=O)COc3nc(-c4ccc(C5(NC(=O)OC(C)(C)C)CCC5)cc4)c(-c4ccccc4)cc32)COC1 | NC1(c2ccc(-c3nc4c(cc3-c3ccccc3)N(Cc3ncc[nH]3)C(=O)CO4)cc2)CCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure for 1-((1H-imidazol-2-yl)methyl)-6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one, tert-butyl(1-(4-(1-((3-methyloxetan-3-yl)methyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (16 mg, 0.03 mmol) was reacted to afford the t... | CC(CO)(CO)CN1C(=O)COc2nc(-c3ccc(C4(N)CCC4)cc3)c(-c3ccccc3)cc21 | null | 79 | null |
1,089,578 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [OH:1][CH:2]([C:5]1[N:6]=[C:7]([C:10]2[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH:13][CH:14]=2)[S:8][CH:9]=1)[CH2:3][OH:4].[Br:22]N1C(=O)CCC1=O.O>O1CCCC1>[Br:22][C:12]1[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([C:7]2[S:8][CH:9]=[C:5]([CH:2]([OH:1])[CH2:3][OH:4]... | CC(C)(C)OC(=O)n1cccc1-c1nc(C(O)CO)cs1 | O=C1CCC(=O)N1Br | null | null | null | null | 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 | 0 | 14 | t-Butyl 2-[4-(1,2-dihydroxyethyl)-1,3-thiazol-2-yl]-1H-pyrrole-1-carboxylate (868 mg, 2.80 mmol) synthesized in Example (9c) was dissolved in tetrahydrofuran (30 mL), and cooled to 0° C. N-Bromosuccinimide (498 mg, 2.80 mmol) was added, and stirring was carried out at room temperature for 14 hours under nitrogen atmosp... | CC(C)(C)OC(=O)n1c(Br)ccc1-c1nc(C(O)CO)cs1 | null | 48.4 | null |
289,837 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24])[NH:8][C:7](=[O:25])[C:6]([C:26]([F:29])([F:28])[F:27])=[CH:5]2.Br[CH2:31][C:32]#[CH:33].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:33]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]... | C#CCBr | Cn1c(C(F)(F)F)cc(=O)n(-c2cc3[nH]c(=O)c(C(F)(F)F)cc3cc2F)c1=O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | These compounds were prepared in a manner analogous to that of Step I of Example 1, using 1.0 gram (0.002 mole) of 3-(6-fluoro-3-trifluoromethylquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil, 0.7 gram (0.005 mole) of 80% 3-bromopropyne, and 0.7 gram (0.005 mole) of potassium carbonate in 40 mL of N,N-dimethylform... | C#CCn1c(=O)c(C(F)(F)F)cc2cc(F)c(-n3c(=O)cc(C(F)(F)F)n(C)c3=O)cc21 | null | 86.7 | null |
1,289,552 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | CS(O[CH2:6][C@H:7]1[CH2:12][N:11]([S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)(=O)=O.[CH:34]1([CH:37]2[CH2:42][S:41](=[O:44])(=[O:43])[CH2:40][CH2:39][NH:38]2)[CH2:36][CH2:35]1>>[C... | CC(O)(c1ccc(N2CCN(S(=O)(=O)c3cccs3)C[C@@H]2COS(C)(=O)=O)cc1)C(F)(F)F | O=S1(=O)CCNC(C2CC2)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 | This compound was synthesized following the procedure outlined for Example 84. The reaction of ((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate (Intermediate B) and 3-cyclopropylthiomorpholine 1,1-dioxide followed by purification via column chrom... | CC(O)(c1ccc(N2CCN(S(=O)(=O)c3cccs3)C[C@@H]2CN2CCS(=O)(=O)CC2C2CC2)cc1)C(F)(F)F | null | null | null |
1,710,163 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | Cl[C:2]1[CH:7]=[C:6]([N:8]([CH:16]2[CH2:18][CH2:17]2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[N:5]2[N:19]=[CH:20][C:21]([CH:22]=[O:23])=[C:4]2[N:3]=1.[OH:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=C... | OB(O)c1cccc(O)c1 | CC(C)(C)OC(=O)N(c1cc(Cl)nc2c(C=O)cnn12)C1CC1 | 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 | COCCOC | CCO | null | null | null | null | null | null | null | null | null | 85 | 1 | To tert-butyl 5-chloro-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (650 mg, 1.93 mmol) in 14 mL of a 2:1 mixture of 1,2-dimethoxyethane/EtOH was added 3-hydroxyphenyl boronic acid (399 mg, 2.89 mmol), tetrakis(triphenylphosphine)palladium(0) (112 mg, 0.096 mmol), and 2M aqueous solution of Na2CO3 (2.9 m... | CC(C)(C)OC(=O)N(c1cc(-c2cccc(O)c2)nc2c(C=O)cnn12)C1CC1 | null | 52.5 | null |
1,399,043 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:4]=2[N:3]=1.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23]>>[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[C:7](/[CH:23]=[CH:22]/[C:... | C=CC(=O)OC | CC(C)(O)Cn1cnc2c(N)nc3ccc(Br)cc3c21 | null | null | null | null | null | null | null | 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 method described in Example 15 Part E can be used to couple 1-(4-amino-8-bromo-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol with methyl acrylate to provide Methyl(2E)-3-[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-8-yl]prop-2-enoate. | COC(=O)/C=C/c1ccc2nc(N)c3ncn(CC(C)(C)O)c3c2c1 | null | null | null |
501,481 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([N+:13]([O-])=O)[C:5]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)([O-])=O.Cl>>[NH2:1][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[C:6]([NH2:13])[C:5]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1 | Cc1ccc(-c2c([N+](=O)[O-])cc([N+](=O)[O-])cc2[N+](=O)[O-])cc1 | null | 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 | 2′,4′,6′-trinitro-4-methylbiphenyl (1) is reacted with stannous chloride and hydrochloric acid to yield 2′,4′,6′-triamino-4-methylbiphenyl (2). | Cc1ccc(-c2c(N)cc(N)cc2N)cc1 | null | null | null |
1,010,334 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.CC([O-])(C)C.[K+].[N:18](OC(C)(C)C)=[O:19]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[N:18][OH:19])[C:10]=2[CH:11]=1 | CC(C)(C)ON=O | Clc1cc2c(cn1)CCCC2 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 12 | 3-Chloro-5,6,7,8-tetrahydro-isoquinoline (Chemische Berichte 1948, 81, 279) (8.82 g; 52.6 mmol) dissolved in THF (65 ml) is added under stirring at room temperature to a solution of KOtBu (11.78 g; 105.2 mmol) in THF (100 ml). The red turbid solution is stirred for 12 hours and then cooled to 0° C. tert-Butyl nitrite (... | ON=C1CCCc2cnc(Cl)cc21 | null | null | null |
1,528,048 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | C[O:2][C:3]([C:5]1[C:6](=[O:27])[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:4].[Li+].[I-]>N1C=CC=CC=1>[CH2:14]([O:13][C:11]([C:10]1[CH:9]=[CH:8][N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C... | CCOC(=O)c1ccn(Cc2ccc(OC)cc2OC)c(=O)c1C(=O)OC | null | null | [I-] | [Li+] | 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 | null | A solution of 1-(2,4-dimethoxy-benzyl)-2-oxo-1,2-dihydro-pyridine-3,4-dicarboxylic acid 4-ethyl ester 3-methyl ester (18.4 g, 49.0 mmol) in 30 mL of pyridine was added to a refluxing mixture of LiI (26.2 g, 196 mmol) in 190 mL of pyridine. The resulting mixture was refluxed for 1 h. After the mixture was cooled to r.t.... | CCOC(=O)c1ccn(Cc2ccc(OC)cc2OC)c(=O)c1C(=O)O | null | 74.6 | null |
1,016,751 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.C1(S([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[C:19]([C:26]3[CH:31]=[CH:30][N:29]=[C:28](Cl)[N:27]=3)=[CH:18]2)(=O)=O)C=CC=CC=1>>[NH:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[C:19]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([N:1]3[CH2:6][CH2:5][CH:4]([NH2:7]... | O=S(=O)(c1ccccc1)n1cc(-c2ccnc(Cl)n2)c2cccnc21 | NC1CCNCC1 | null | null | null | null | null | null | null | 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 the procedure of example 1, piperidin-4-ylamine (540 mg) was reacted with compound 1f (500 mg) to provide compound 62 (285 mg, 72%). 1H NMR (400MHz, DMSO) δ 8.70 (d, 1 H), 8.40 (s, 1 H), 8.25 (m, 1 H), 8.20 (d, 1 H), 7.20 (m, 1 H), 7.05 (d, 1 H), 4.60 (d, 2 H), 3.05 (m, 2 H), 2.85 (m, 1 H), 1.85 (m, 2 H), 1.25 (m... | NC1CCN(c2nccc(-c3c[nH]c4ncccc34)n2)CC1 | null | 71.8 | null |
1,138,114 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [CH:1]1([CH:6]2[C:15]3[C:14](=[O:16])[CH2:13][C:12]([CH3:18])([CH3:17])[CH2:11][C:10]=3[NH:9][C:8]([CH:19]([CH3:21])[CH3:20])=[C:7]2[C:22](=[O:33])[C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[CH:1]1([C:6]2[C:15]3[C:14](... | CC(C)C1=C(C(=O)c2ccc(C(F)(F)F)cc2)C(C2CCCC2)C2=C(CC(C)(C)CC2=O)N1 | null | null | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | null | 4.0 g (8.7 mmol) of the compound from Example 1A are dissolved in 100 ml of dichloro-methane, and 2.17 g (9.6 mmol, 1.1 eq.) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) are added a little at a time at 0° C. With stirring, the mixture is warmed to room temperature over a period of 3 h. The mixture is concentrated... | CC(C)c1nc2c(c(C3CCCC3)c1C(=O)c1ccc(C(F)(F)F)cc1)C(=O)CC(C)(C)C2 | null | null | null |
788,473 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | [F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:26])[C:19]([O:21][CH2:22][CH:23]4[CH2:25][O:24]4)=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:27])[NH:6]2.[CH3:28][S:29]([O-:31])=[O:30].[Na+]>CS(C)=O>[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:26])[C:19]([O:21][CH2:22][CH:... | Cc1cc2c(F)c(Oc3ncnn4cc(OCC5CO5)c(C)c34)ccc2[nH]1 | CS(=O)[O-] | null | [Na+] | 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 | A mixture of Example 2 (10 mg, 0.027 mmol) and sodium methanesulfinate (120 mg, 85%, 1.0 mmol) in DMSO was heated at 105° C. for 1 hr. The mixture was concentrated and purified by chromatography on silica gel eluting with 5% methanol in ethyl acetate to provide the title compound (5.5 mg, 45%) as a white solid. MS: (M+... | Cc1cc2c(F)c(Oc3ncnn4cc(OCC(O)CS(C)(=O)=O)c(C)c34)ccc2[nH]1 | null | 45.4 | null |
1,382,545 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [F:1][C:2]([F:11])([F:10])[CH:3]([CH2:8][CH3:9])[CH2:4][C:5]([OH:7])=[O:6].[CH3:12][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[CH3:12][O:6][C:5](=[O:7])[CH2:4][CH:3]([C:2]([F:10])([F:11])[F:1])[CH2:8][CH3:9] | CCC(CC(=O)O)C(F)(F)F | C[Si](C)(C)C=[N+]=[N-] | 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 | To a stirred solution of Example 1D (250 mg, 1.47 mmol) in dichloromethane (10 mL) and methanol (0.25 mL), under nitrogen atmosphere, trimethylsilyldiazomethane (2.0 M solution in diethyl ether) (2.1 mL, 4.19 mmol) was added drop wise at 0° C. The reaction mixture was stirred keeping the temperature below 5° C. for 1 h... | CCC(CC(=O)OC)C(F)(F)F | null | 92.3 | null |
1,634,852 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:17][CH2:18][CH:19]([PH:21](=[O:25])[O:22][CH2:23][CH3:24])[CH3:20])=[CH:15][C:14]=2[O:28][CH3:29])[N:3]=1.[NH2:30][C:31]1[C:32]([C:38]([NH:40][CH3:41])=[O:39])=[N:33][C:34]([Br:37])=[CH:35][CH:36]=1.C(O)(C(F)(F)F)=O>>[B... | CCO[PH](=O)C(C)CCc1ccc(Nc2ncc(C(F)(F)F)c(Cl)n2)c(OC)c1 | CNC(=O)c1nc(Br)ccc1N | 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 | 80 | null | A solution of ethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)propan-2-ylphosphinate (Compound 68D, 1.00 g, 2.21 mmol) and 3-amino-6-bromo-N-methylpyridine-2-carboxamide (Compound 6D, 0.516 g, 2.24 mmol) in TFE (11.71 mL) was charged with TFA (0.341 mL, 4.43 mmol). The reaction mixture was ... | CCO[PH](=O)C(C)CCc1ccc(Nc2ncc(C(F)(F)F)c(Nc3ccc(Br)nc3C(=O)NC)n2)c(OC)c1 | null | 60.6 | null |
305,262 | ord_dataset-180e296d6d6245638d4d22a59120ea01 | null | 1995-01-01T00:02:00 | true | [Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([Cl:10])=[CH:4][C:3]=1[CH2:11]O.P(Br)(Br)[Br:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([Cl:10])=[CH:4][C:3]=1[CH2:11][Br:14] | COc1cc(Cl)cc(CO)c1Cl | BrP(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | By the method of Example 1, Step B, 13.95 grams (0.0674 mole) of 2,5-dichloro-3-methoxyphenylmethanol and 7.295 grams (0.270 mole) of phosphorus tribromide were reacted in toluene, yielding 15.76 grams of 2,5-dichloro-3-methoxyphenylmethyl bromide as an oil. The NMR spectrum was consistent with the proposed structure. | COc1cc(Cl)cc(CBr)c1Cl | null | 86.6 | null |
1,704,827 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH3:1][C:2]1[C:7]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[N:14][N:15]([CH2:17][C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[C:23]([CH3:28])[CH:22]=[CH:21]4)[CH:16]=2)=[O:11])=[C:6]([CH3:29])[N:5]=[C:4]([NH:30]C(=O)OC(C)(C)C)[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][C:4]1[N:5]=[C:6]([CH3:29])[C:7]([CH2:8][NH:9][C:... | Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(NC(=O)OC(C)(C)C)nc4C)nn3)ccc2n1 | 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 | 23 | 8 | To a solution of tert-butyl (4,6-dimethyl-5-((1-((2-methylquinolin-6-yl)methyl)-1H-1,2,3-triazole-4-carboxamido)methyl)pyridin-2-yl)carbamate (131.9 mg, 0.263 mmol) in DCM (1.2 ml) was added TFA (0.405 ml, 5.26 mmol). Reaction mixture was stirred overnight at 23° C. Reaction mixture was evaporated to afford the crude m... | Cc1ccc2cc(Cn3cc(C(=O)NCc4c(C)cc(N)nc4C)nn3)ccc2n1 | null | null | null |
628,068 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [CH3:1][C:2]1[N:3]([C:7]2[O:8][C:9]([CH2:22][CH2:23][CH2:24][OH:25])=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[N:11]=2)[CH:4]=[CH:5][N:6]=1.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:1][C:2]1[N:3]([C:7]2... | Cc1nccn1-c1nc(-c2ccc(C(F)(F)F)cc2)c(CCCO)o1 | Cc1ccccc1O | null | CCCCP(CCCC)CCCC | O=C(N=NC(=O)N1CCCCC1)N1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1 | To a mixture of 2-(2-methyl-1-imidazolyl)-4-(4-trifluoromethylphenyl)-5-oxazolepropanol (700 mg), 2-methylphenol (432 mg), tributylphosphine (607 mg) and tetrahydrofuran (10 mL) was added 1,1′-(azodicarbonyl)dipiperidine (750 mg) at room temperature and the mixture was stirred for 1 h. The reaction mixture was concentr... | Cc1ccccc1OCCCc1oc(-n2ccnc2C)nc1-c1ccc(C(F)(F)F)cc1 | null | null | null |
803,468 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH:14]([NH:17][NH:18][C:19](=[O:31])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:22][CH:21]=1)([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:1... | O=C(O)COc1ccc(F)cc1Br | COCCOc1ccc(C(=O)NNC(C)C)cc1 | null | Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | A solution of (2-bromo-4-fluoro-phenoxy)-acetic acid (164 mg, 0.66 mmol) and 4-(2-methoxy-ethoxy)-benzoic acid-N′-isopropyl hydrazide (200 mg, 0.79 mmol) in DMF (5 ml) was treated with diisopropylethyl amine (0.29 mL, 1.65 mmol) and PyBroP (462 mg, 0.99 mmol) at room temperature overnight. The reaction mixture was part... | COCCOc1ccc(C(=O)NN(C(=O)COc2ccc(F)cc2Br)C(C)C)cc1 | null | 63.3 | null |
1,105,046 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH:1]1([CH2:7][C:8]2[S:12][C:11]([NH:13][C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21]C)[C:18]([O:23]C)=[C:17]([O:25]C)[CH:16]=3)=[N:10][C:9]=2[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>>[CH:1]1([CH2:7][C:8]2[S:12][C:11]([NH:13][C:14](=[O:27])[C:15]3[CH:16]=[C:... | COc1cc(C(=O)Nc2nc(-c3ccc(O)cc3)c(CC3CCCCC3)s2)cc(OC)c1OC | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A procedure similar to that in Example 7 was used. N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide prepared in Example 50 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to obtain a product as a white solid in a yield o... | O=C(Nc1nc(-c2ccc(O)cc2)c(CC2CCCCC2)s1)c1cc(O)c(O)c(O)c1 | null | 55.8 | null |
424,168 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:... | O=C=Nc1ccccc1 | CC(C)(C)OC(=O)NCC1CCN(CCCCCN)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 15 | 5-(4-tert-Butoxycarbonylaminomethylpiperidin-1-yl)pentylamine (2.00 g) was dissolved in methylene chloride (80 ml) and phenyl isocyanate (0.80 ml) was dropwise added under ice-cooling. The mixture was stirred at room temperature for 15 hr, and the reaction mixture was concentrated under reduced pressure to give 4-tert-... | CC(C)(C)OC(=O)NCC1CCN(CCCCCNC(=O)Nc2ccccc2)CC1 | null | null | null |
149,186 | ord_dataset-f222e615b1f74f0fabef9cd9b98516b7 | null | 1986-01-01T00:10:00 | true | ON=[C:3]([CH3:17])[C:4](=[N:12][NH:13][C:14]([NH2:16])=[S:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].C>O.CO>[CH3:17][C:3]1[C:4]([C:5]2[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=2)=[N:12][NH:13][C:14](=[S:15])[N:16]=1 | CC(=NO)C(=NNC(N)=S)c1cccc(C)c1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-hydroxyimino-3'-methylpropiophenone thiosemicarbazone (5 g) and potassium carbonate (6.1 g) in water (44 ml) was refluxed for 4 hours under nitrogen atmosphere. The reaction mixture was treated with activated charcoal and filtered by suction. The filtrate was acidified with diluted hydrochloric acid, and... | Cc1cccc(-c2n[nH]c(=S)nc2C)c1 | null | 115.2 | null |
1,304,297 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][CH3:8])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:21]1[S:22][C:23]([CH:27]=[O:28])=[C:24]([Cl:26])[N:25]=1>O1CCCC1>[Cl:26][C:24]1[N:25]=[C:21]([N:7]([CH2:6][C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:8])[S:22][C:23]=1[CH:27]=[O:28] | O=Cc1sc(Cl)nc1Cl | CNCc1ccc(Cl)cc1 | 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 | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of (4-chloro-benzyl)-methyl-amine (550, 2 g, 0.01 mol) and N,N-diisopropylethylamine (4 mL, 0.03 mol) in tetrahydrofuran (50 mL) was added 2,4-dichloro-thiazole-5-carbaldehyde (93, 3 g, 0.01 mmol) in tetrahydrofuran (20 mL) at room temperature. The reaction mixture was stirred at room temperature overnigh... | CN(Cc1ccc(Cl)cc1)c1nc(Cl)c(C=O)s1 | null | 119,525.2 | null |
200,100 | ord_dataset-aa9e93ade540499c920a9c3b18e8edaa | null | 1989-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[N:8]([CH:13]=[CH:14][CH:15]=3)[N:9]([CH3:12])[C:10]=2[CH:11]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:35]N1C(=O)CCC1=O.[Al]>C1COCC1>[Br:35][C:13]1[N:8]2[N:9]([CH3:12])[C:10]3[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[C:6](=[O:16])[C:7]2=[CH:15][CH:14]=1 | O=C1CCC(=O)N1Br | Cn1c2cc(Cl)ccc2c(=O)c2cccn21 | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | [Al] | 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 | 24 | To a solution of 7-chloro-5-methylpyrrolo[1,2-b]cinnolin-10(5H)-one (6.0 g) and a catalytic amount of dibenzoyl peroxide in 100 ml of THF was added portionwise N-bromosuccinimide (4.63 g) over 15 min. The flask was covered with aluminum foil and the solution was stirred at room temperature for 24 hrs. The solution was ... | Cn1c2cc(Cl)ccc2c(=O)c2ccc(Br)n21 | null | 88.4 | null |
1,434,532 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [CH3:1][C:2]([C:12]1[C:20]2[O:19][CH2:18][CH2:17][C:16]=2[CH:15]=[C:14]([C:21]2[CH:22]=[N:23][CH:24]=[N:25][CH:26]=2)[CH:13]=1)([CH3:11])[CH2:3][C:4]1([C:7]([F:10])([F:9])[F:8])[CH2:6][O:5]1.[NH:27]1[C:35]2[CH2:34][CH2:33][CH2:32][C:31](=[O:36])[C:30]=2[CH:29]=[CH:28]1.[O-]CC.[Na+]>C(O)C>[OH:5][C:4]([C:7]([F:10])([F:8]... | CC(C)(CC1(C(F)(F)F)CO1)c1cc(-c2cncnc2)cc2c1OCC2 | O=C1CCCc2[nH]ccc21 | 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 | 85 | null | To a suspension of 5-{7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran-5-yl}pyrimidine (56.0 mg, 0.15 mmol) and 1,5,6,7-tetrahydroindol-4-one (41.6 mg, 0.31 mmol) in 1.0 mL of anhydrous ethanol was added sodium ethoxide solution (0.057 mL, 21 wt. % in ethanol). The reaction mixture was heated a... | CC(C)(CC(O)(Cn1ccc2c1CCCC2=O)C(F)(F)F)c1cc(-c2cncnc2)cc2c1OCC2 | null | 56.1 | null |
752,203 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:33]([O-])=O)=[C:6]([C:8]([CH3:32])([CH3:31])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[O:23])[O:21][N:20]=[C:19]([CH3:24])[C:18]=3[CH:25]=2)=[O:12])[CH:7]=1.O1CCCC1>C(O)(=O)C.[Fe]>[NH2:33][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7... | Cc1noc(=O)c2ccc(NC(=O)C(O)(CC(C)(C)c3cc(F)ccc3[N+](=O)[O-])C(F)(F)F)cc12 | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 16 | 42 mg of 6-[4-(5-fluoro-2-nitrophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleroylamino]-4-methyl-2,3-benzoxazin-1-one is dissolved in 1 ml of acetic acid and 1 ml of tetrahydrofuran b, mixed with 22.5 mg of iron powder and stirred for 16 hours at room temperature. It is suctioned off on diatomaceous earth, concentrat... | Cc1noc(=O)c2ccc(NC(=O)C(O)(CC(C)(C)c3cc(F)ccc3N)C(F)(F)F)cc12 | null | 25.3 | null |
227,630 | ord_dataset-d98d003e9abb4b579746c5a361466e14 | null | 1991-01-01T00:05:00 | true | O=[C:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OC(=O)C)(=O)C>C1C=CC=CC=1.[Zn]>[CH2:3]([C:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3... | CCOC(=O)CBr | CCCCCCCCCCCCC(=O)c1coc([Si](C)(C)C)c1 | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)OC(C)=O | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 14 | A mixture of 4-(1-ketotridecyl)-2-trimethylsilylfuran (Compound 26, 84.5 mg, 0.25 mmol), zinc (100 mg, 1.53 mmol) and ethyl bromoacetate (105 mg, 0.63 mmol) in benzene (6 ml) was refluxed for 2 hours. After cooling to 0°, acetic anhydride (83 ul, 0.88 mmol) was added. Stirring was continued for 14 hours while the cooli... | CCCCCCCCCCCCC(=CC(=O)OCC)c1coc([Si](C)(C)C)c1 | null | null | null |
1,762,742 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH:1]1([O:7][CH2:8][C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:12]SCl>>[CH:1]1([O:7][CH2:8][C:9]([Cl:12])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | O=C(O)COC1CCCCC1 | ClSCl | null | null | null | null | null | 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 | A mixture of 2-(cyclohexyloxy)acetic acid (0.90 g, 5.69 mmol) and dichlorosulfane (10 mL) was refluxed for 2 h. The mixture was cooled to rt and concentrated in vacuo to give the title compound as yellow oil, which was used for next step without further purification. | O=C(Cl)COC1CCCCC1 | null | null | null |
1,458,582 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[N:18]([C:21]1[C:22]([CH3:30])=[CH:23][C:24]([N:27]([CH3:29])[CH3:28])=[N:25][CH:26]=1)=[C:19]=[S:20]>O1CCCC1>[Cl:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([NH:13][CH2:14][CH2:15... | Cc1cc(N(C)C)ncc1N=C=S | COC(=O)c1ccc(Cl)c(N)c1NCCCO | 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 | 70 | 7 | A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (4.00 g, 15.5 mmol) and 5-isothiocyanato-N,N,4-trimethylpyridin-2-amine (8.96 g, 46.4 mmol) in tetrahydrofuran (30 mL) was stirred at 70° C. for 7 hr. The mixture was concentrated in vacuo, and the residue was purified by flash column chromatograph... | COC(=O)c1ccc(Cl)c(NC(=S)Nc2cnc(N(C)C)cc2C)c1NCCCO | null | null | null |
882,087 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:17][C:3]=1[O:4][C:5]1[C:6]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:41](O)[CH2:42][CH2:43][CH2:44]C>O>[Cl:1][C:2... | COC(=O)COc1ncccc1Oc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)c(F)cc1Cl | CCCCCO | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 100 | 1.5 | A mixture of 0.30 g of methyl [3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-pyridyloxy]acetate (compound a-6), 0.06 g of sodium carbonate, and 3.0 ml of n-pentanol was stirred at 100° C. for 1.5 hours. After cooling to room temperature, the reaction mixture ... | CCCCCOC(=O)COc1ncccc1Oc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)c(F)cc1Cl | null | null | null |
815,734 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | C(OC([NH:8][C:9]([CH3:36])([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([C:22]2([C:27]#[N:28])[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:21]=1)[C:16]([OH:18])=O)=O)(C)(C)C.[Cl:37][C:38]1[CH:39]=[C:40]([CH:44]([NH2:46])[CH3:45])[CH:41]=[CH:42][CH:43]=1>>[NH... | CC(COCc1cc(C(=O)O)cc(C2(C#N)CCCC2)c1)(Cc1ccccc1)NC(=O)OC(C)(C)C | CC(N)c1cccc(Cl)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 | Prepared from 3-((2-tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoic acid and 1-(3-chlorophenyl)ethanamine using a similar procedure as described for the preparation of Example 20. HRMS ES calculated for C32H36ClN3O2: 530.2569, found: 530.2565. | CC(NC(=O)c1cc(COCC(C)(N)Cc2ccccc2)cc(C2(C#N)CCCC2)c1)c1cccc(Cl)c1 | null | null | null |
47,807 | ord_dataset-b43eb0158fd54801957aaa07bbdf3057 | null | 1978-01-01T00:11:00 | true | [C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[N:15]1[C:19](=[O:20])[C:18]2=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=[C:17]2[C:16]1=[O:26])(=[O:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Rh]>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:7]=1[N:15]1[C:19](=[O:20])[C:18]2=[CH:21][C:22]([Cl... | [H][H] | CC(=O)OCc1cc([N+](=O)[O-])ccc1N1C(=O)c2ccc(Cl)cc2C1=O | null | [Rh] | 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 | null | null | The solution of 300 mg of N-(2-acetoxymethyl-4-nitrophenyl)-4-chlorophthalimide in 35 ml of ethyl acetate is hydrogenated with 200 mg of 5% rhodium on carbon at 2.5 atmospheres of hydrogen pressure for 3 hours. After filtration from the catalyst, the residue is crystallized from ethyl acetate-hexane to give the N-(2-ac... | CC(=O)OCc1cc(N)ccc1N1C(=O)c2ccc(Cl)cc2C1=O | null | null | null |
667,952 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[NH2:24][CH2:25][CH2:26][S:27][CH2:28][CH2:29][OH:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][NH:24][CH2... | O=Cc1ccc(Cl)c(C(=O)NCC23CC4CC(CC(C4)C2)C3)c1 | NCCSCCO | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the method described in Example 2 from 2-chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.800 g, Example 1b), 2-(2-aminoethylthio)ethanol (0.584 g) and sodium triacetoxyborohydride (0.715 g) in 1,2-dichloroethane (15 ml). After work-up, the residue was purified by NPHPLC elutin... | O=C(NCC12CC3CC(CC(C3)C1)C2)c1cc(CNCCSCCO)ccc1Cl | null | 50.9 | null |
1,562,712 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=3)[CH:12]=[C:6]2[C:5]=1[NH:19][C@@H:20]1[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][C@H:21]1[CH2:33][CH3:34])(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl>[CH2:33]([C@H:21]1[C@H:20]([NH:19][C:5]2[C:6]3[N:7]([CH:10]=[C:11]([C:13]4[CH:14]... | CC[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1Nc1c(C(N)=O)cnn2cc(-c3cnn(C)c3)cc12 | 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 | 1 | To a solution of (3R,4R)-tert-butyl 4-((3-carbamoyl-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3-ethylpiperidine-1-carboxylate (288 mg, 0.618 mmol) in dichloromethane (5.0 ml) cooled to 0° C. was added trifluoroacetic acid (288 μl, 3.74 mmol). The reaction was allowed to warm to room temperature an... | CC[C@@H]1CNCC[C@H]1Nc1c(C(N)=O)cnn2cc(-c3cnn(C)c3)cc12 | null | 100 | null |
215,854 | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | null | 1990-01-01T00:09:00 | true | [BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:17]=[CH:18][C:19]3[CH2:24][C:23](=[O:25])[N:22]([CH3:26])[C:20]=3[N:21]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[C:20]([NH:22][CH3:26])[C:19]([CH2:24][CH2:23][OH:25])=[CH:18][N:17]... | CN1C(=O)Cc2cnc(N3CCN(Cc4ccccc4)CC3)nc21 | null | null | [BH4-] | [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 | null | null | Sodium borohydride (2.24 g) was added to 8.0 g of 2-(4-benzylpiperazino)-5,6-dihydro-7-methyl-6-oxo-(7H)pyrrolo[2,3-d]pyrimidine (produced in accordance with Referential Example 54 of Japanese Laid-Open Patent Publication No. 140568/1986) and 400 ml of ethanol, and the mixture was heated under reflux for 1.5 hours. The... | CNc1nc(N2CCN(Cc3ccccc3)CC2)ncc1CCO | null | 29.6 | null |
1,079,425 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].Cl[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:25][C:24]([F:26])([F:27])[C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([CH2:11][... | FC(F)(F)c1ccc(-c2ccc(CCl)cc2)cc1 | OCc1ccccc1O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 4.59 g (36.94 mmol) of 2-hydroxybenzyl alcohol in 200 ml of dry acetonitrile is mixed with 10 g (36.94 mmol) of 4-chloromethyl-4′-trifluoromethylbiphenyl from Example 23A and 6.13 g (44.33 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then concentrated to dryness... | OCc1ccccc1OCc1ccc(-c2ccc(C(F)(F)F)cc2)cc1 | null | 89.1 | null |
182,752 | ord_dataset-f25e1b7f8ef54305a5170f5395a768c7 | null | 1989-01-01T00:01:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[N:11][OH:12])[CH2:8][C:9]#[CH:10])[CH:2]=1.[I-].[CH3:14][N+]1C=CC=CC=1.[BH4-].[Na+]>>[CH3:14][N:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7](=[N:11][OH:12])[CH2:8][C:9]#[CH:10])[CH2:2]1 | C#CCC(=NO)c1cccnc1 | C[n+]1ccccc1 | null | [BH4-] | [I-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Employing the general method of Example 6 above, 2.12 g (12.2 mmol) of 1-(3-pyridinyl)-3-butyne-1-one oxime were converted to the corresponding 1-methyl pyridinium iodide and subsequently reduced by the action of sodium borohydride to produce 1.2 g of 1-(1,2,5,6-tetrahydro-1-methyl-3-pyridinyl)-3-butyne-1-one oxime whi... | C#CCC(=NO)C1=CCCN(C)C1 | null | null | null |
193,401 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]([CH2:19][CH2:20][CH2:21][CH:22]=[CH:23][C:24]([OH:26])=[O:25])=[N:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]([CH2:19][CH2:20]... | [H][H] | O=C(O)C=CCCCc1nn(-c2ccc([N+](=O)[O-])cc2)c2c1CCCC2 | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 6-[4,5,6,7-tetrahydro-1-(4-nitrophenyl)-1H-inda-zol-3-yl]hexenoic acid n acetic acid (75 ml) was treated with 10% palladium/C (0.80 g) and reduced at 40 psi hydrogen pressure for 2 hours. The catalyst was filtered and the filtrate was evaporated to yield crude 1-[4-(amino)phenyl]-4,5,6,7-tetrahydro-1H-ind... | Nc1ccc(-n2nc(CCCCCC(=O)O)c3c2CCCC3)cc1 | null | null | null |
165,963 | ord_dataset-5c25f386f4664070a72d578feacedf86 | null | 1987-01-01T00:12:00 | true | C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([CH3:19])[CH:7]=[C:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:9]=2)[N:4]=1.[OH-].[Na+]>Cl>[CH3:19][C:6]1[CH:7]=[C:8]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:9]=[C:10]2[C:5]=1[NH:4][C:3](=[O:2])[CH:12]=[CH:11]2 | COc1ccc2cc(-c3cccnc3)cc(C)c2n1 | null | null | Cl | [Na+] | [OH-] | null | null | null | 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 stirred solution of 2-methoxy-8-methyl-6-(3-pyridyl)quinoline (1.07 g) in 5M hydrochloric acid (10 cm3) was heated under reflux for 2.5 hours and then cooled. The cooled solution was basified to pH 9 with 2M aqueous sodium hydroxide, extracted with chloroform:methanol 9:1 (4×100 cm3), and the combined and dried (MgSO... | Cc1cc(-c2cccnc2)cc2ccc(=O)[nH]c12 | null | null | null |
464,291 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | C([Li])CCC.C(NC(C)C)(C)C.[CH:13]1([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:14]1.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[CH:13]1(/[CH:16]=[C:17](\[O:19][CH2:20][CH3:21])/[O:18][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:14]1 | CCOC(=O)CC1CC1 | C[Si](C)(C)Cl | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)NC(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | -75 | 0.5 | A solution of n-butyllithium in hexanes (1.6M, 26 ml) was added with stirring to a solution of diisopropylamine (6.2 ml) in tetrahydrofuran (8 ml) at below -25° C. under nitrogen. After 30 min, the mixture was cooled to -75° C. and ethyl cyclopropylacetate (4.5 g) added dropwise keeping the temperature below -65° C. Th... | CCO/C(=C\C1CC1)O[Si](C)(C)C | null | null | null |
1,431,823 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | Cl[C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]2[N:5]=[CH:4][C:3]=1[C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)=[O:17].[NH2:30][C:31]1[C:35]([CH3:36])=[CH:34][S:33][CH:32]=1>>[CH2:14]([O:13][C:11]([C:10]1[CH:9]=[N:8][N:7]2[C:2]([NH... | Cc1cscc1N | CCOC(=O)c1cnn2c(Cl)c(C(=O)N3CCC(c4ccccc4)CC3)cnc12 | null | null | null | null | null | null | null | 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 the same manner as in Example 19, step 5 and using 7-chloro-3-ethoxycarbonyl-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine (0.20 g, 0.48 mmol) obtained in Example 19, step 4 and 3-amino-4-methylthiophene (0.110 g, 0.97 mmol), the title compound (0.099 g, 42%) was obtained. | CCOC(=O)c1cnn2c(Nc3cscc3C)c(C(=O)N3CCC(c4ccccc4)CC3)cnc12 | null | 42.1 | null |
1,479,254 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[S:25](=[O:39])(=[O:38])[NH:26][CH2:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([CH3:37])[CH:32]=[CH:31]2)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[Cl:13][C:14]1[CH:15]=[C:16]([CH:... | CCOC(=O)c1ccc(S(=O)(=O)NCc2ccc3c(ccn3C)c2)c(Cl)c1 | FC(F)(F)c1cnc(Cl)c(Cl)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 titled compound was prepared according to the procedure described in step-2 of Example 1 from 2,3-dichloro-5-(trifluoromethyl)pyridine and ethyl 3-chloro-4-(N-((1-methyl-1H-indol-5-yl)methyl)sulfamoyl)benzoate (step-1 of Example 8). | CCOC(=O)c1ccc(S(=O)(=O)N(Cc2ccc3c(ccn3C)c2)c2ncc(C(F)(F)F)cc2Cl)c(Cl)c1 | null | null | null |
1,454,452 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3] | CC(C)(C)OC(=O)NCCCO | 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 | CCOCC | null | null | null | null | null | null | null | null | null | null | null | A solution of (3-hydroxypropyl)-carbamic acid tert-butyl ester (0.60 g, 3.4 mmol) in anhydrous CH2Cl2 (17 mL) was treated with Dess-Martin reagent (1.74 g, 4.1 mmol) for 3 hours at room temperature. The reaction mixture was diluted with Et2O (30 mL) and washed with a 20% aqueous solution of sodium thiosulfate (15 mL) f... | CC(C)(C)OC(=O)NCCC=O | null | 91.7 | null |
187,185 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:19])[C:15]([O:17][CH3:18])=[O:16])[CH:10]=[CH:11][CH:12]=1.O>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:19])[C:15]([O:17][CH3:18])=[O:16])[CH:10]=[CH:11][CH:12]=1 | COC(=O)C(=O)Nc1cccc(OC)c1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | 25 | 5 | 5 g of boron tribromide are added dropwise to a solution, cooled to -78° C., of 2 g of methyl N-(3-methoxyphenyl)-oxamate in 20 ml of methylene chloride in the course of 5 minutes. The mixture is stirred at room temperature for 5 hours, 5 ml of water are added, with cooling, and the organic phase is separated off. Dryi... | COC(=O)C(=O)Nc1cccc(O)c1 | null | null | null |
641,196 | ord_dataset-1c0bae7388cf460091d56129e95b3145 | null | 2004-01-01T00:06:00 | true | Cl[C:2]1[CH:3]=[C:4]([CH2:18][C:19]([O:21]C)=[O:20])[CH:5]=[CH:6][C:7]=1NC(NC1C=CC=CC=1)=O.[OH-].[Na+]>C1COCC1>[C:4]1([CH2:18][C:19]([OH:21])=[O:20])[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1 | COC(=O)Cc1ccc(NC(=O)Nc2ccccc2)c(Cl)c1 | null | null | [Na+] | [OH-] | 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 | 20 | To a stirred solution of methyl 3-chloro-4-(N′-phenylureido)phenylacetate (1.79 g, 5.62 mmol) in THF (30 ml) was added 0.25 N NaOH (30 ml). After stirring at room temperature for 20 h, the solvent was concentrated in vacuo. The residue was triturated by the addition of 1 N HCl and dried at 60° C. for 2 days under a red... | O=C(O)Cc1ccccc1 | null | 206.5 | null |
1,460,205 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl.[C:2]1([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C@@H:19]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:25][CH:2... | N[C@@H](COCc1ccccc1)C(=O)Nc1ccc(Oc2ccc(F)cc2)cc1 | O=C(O)CN1CCN(c2ccccc2)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 | Proceeding as in Example 1, but substituting 2-(4-phenylpiperazin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)propanamide, gave Compound 225, (S)-3-(benzyloxy)-N-(4-(4-fluorophenoxy)phenyl)-2-(2-(4-phenylpiperazin-1-yl)acetamido)propanamide (13.4 mg, 28.7%); Major isomer: 1... | O=C(CN1CCN(c2ccccc2)CC1)N[C@@H](COCc1ccccc1)C(=O)Nc1ccc(Oc2ccc(F)cc2)cc1 | null | 28.7 | null |
1,477,200 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [Li+].[Cl-:2].[C:3]1([CH2:9][CH2:10][CH2:11]O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>>[C:3]1([CH2:9][CH2:10][CH2:11][Cl:2])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1 | [Cl-] | OCCCc1ccccc1 | null | [Li+] | null | null | null | null | null | 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 rates of reaction of LiCl with glycol-containing sulfonate esters 2 were compared with their corresponding ortho-methylcarboxyphenyl sulfonates 3 and tosylates 4 (Table 1). In each case, substrates 2 reacted significantly faster than sulfonates 3. For example, the NALG derivative of 3-phenyl propanol (2a) reacted w... | ClCCCc1ccccc1 | null | 98 | null |
289,593 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [C:1]([NH:4][CH:5]1[C:10]2[CH:11]=[CH:12][S:13][C:9]=2[S:8](=[O:15])(=[O:14])[NH:7][CH2:6]1)(=O)[CH3:2].CO>O1CCCC1>[CH2:1]([NH:4][CH:5]1[C:10]2[CH:11]=[CH:12][S:13][C:9]=2[S:8](=[O:14])(=[O:15])[NH:7][CH2:6]1)[CH3:2] | CC(=O)NC1CNS(=O)(=O)c2sccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 70 | 4 | A suspension of 4-acetamido-3,4-dihydro-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (4.93 g, 0.02 mol) in tetrahydrofuran (50 ml) was heated in an oil bath at 70° C. Borane-dimethyl sulfide complex (20.0 ml of 10.0M, 0.20 mol) was added dropwise over 1/2 hour and the mixture was stirred at 70° C. for 4 hrs. The mixture w... | CCNC1CNS(=O)(=O)c2sccc21 | null | 96 | null |
6,140 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [CH3:1][C:2]([C:4]1[C:5]([OH:11])=[CH:6][CH:7]=[CH:8][C:9]=1[OH:10])=[O:3].[C:12]1([O:19][CH2:20][CH:21]2[O:23][CH2:22]2)[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(OCCO)C>[C:2]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:22][CH:21]([OH:23])[CH2:20][O:19][C:12]1[CH:1... | Cc1cccc(OCC2CO2)c1 | CC(=O)c1c(O)cccc1O | null | C[N+](C)(C)Cc1ccccc1 | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2,6-dihydroxyacetophenone (15.2 g), m-cresylglycidyl ether (16.4 g) and benzyltrimethylammonium hydroxide (10 drops of a 40% solution) in 2-ethoxyethanol (75 ml) was heated under reflux for 48 hours. The solvent was then removed under reduced pressure to give 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-m-cr... | CC(=O)c1c(O)cccc1OCC(O)COc1cccc(C)c1 | null | 99.7 | null |
1,268,808 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[C:4]([O:18][CH3:19])[CH:3]=1.[Cl-].[NH4+]>CO.O.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])=[C:4]([O:18][CH3:19])[CH:3]=1 | COc1cc(F)ccc1Oc1ccccc1[N+](=O)[O-] | null | null | [Cl-] | [NH4+] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of title compound 90 (9.32 g, 35.4 mmol) in MeOH (30 mL) and water (5 mL) was added ammonium chloride (3.79 g, 70.8 mmol) and zinc chloride (20.83 g, 319 mmol) and the reaction mixture was heated to reflux for 2 hours. The mixture was cooled to room temperature and filtered and the solvent removed. The re... | COc1cc(F)ccc1Oc1ccccc1N | null | 100.5 | null |
1,208,751 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)([O-:3])=[O:2].OS(O)(=O)=O.[CH3:18][CH2:19]O>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:18]([O:11][C:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)=[O:12])[CH3:19] | CCO | O=C(O)c1ccc([N+](=O)[O-])cn1 | null | O=C([O-])O | O=S(=O)(O)O | [Na+] | 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 | null | 1.5 | A mixture of 5-nitro-pyridine-2-carboxylic acid (Step 39.5) (5.74 g, 34.2 mmol), H2SO4 (1 mL) and EtOH (50 mL) was stirred for 1.5 h at reflux. The residue was diluted with EtOAc and saturated solution of NaHCO3. The aqueous layer was separated and extracted with EtOAc. The organic phase was washed with H2O and brine, ... | CCOC(=O)c1ccc([N+](=O)[O-])cn1 | null | null | null |
1,106,888 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@@H:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:15]([C:24](O)=[O:25])[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OC)=O.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@@H:16]([C:18]4[CH:19... | O=C(O)[C@@H]1CN(C(=O)C2(c3ccc(Cl)cc3)CC2)C[C@H]1c1ccccc1 | null | null | COC(=O)Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | -15 | 0.33 | To a solution of (3S,4R)-1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}-4-phenylpyrrolidine-3-carboxylic acid (80 mg, 0.0002 mol, example 355) in tetrahydrofuran (2 mL, 0.02 mol) were added triethylamine (0.0316 mL, 0.000227 mol) and methyl chloroformate (20.0 μL, 0.000260 mol) at −15° C. The mixture was stirred at −15° C... | O=C(N1C[C@@H](CO)[C@H](c2ccccc2)C1)C1(c2ccc(Cl)cc2)CC1 | null | null | null |
1,061,044 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [Cl:1][CH2:2][CH2:3][S:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])=[CH:7][C:6]=1[N+:18]([O-])=O>CC(O)=O.[Fe]>[NH2:18][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][C:5]=1[S:4][CH2:3][CH2:2][Cl:1])[C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10] | CC(C)CNC(=O)c1ccc(SCCCl)c([N+](=O)[O-])c1 | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 70 | 1 | To a solution of 4-(2-chloroethylthio)-N-isobutyl-3-nitrobenzamide (2.38 g, 8.32 mmol) in AcOH (100 mL) was added iron (1.859 g, 33.3 mmol). The mixture was heated to 70° C. and the reaction was allowed to stir for 1 hour. The reaction turned from a dark solution to a light grey slurry. LCMS analysis of the reaction mi... | CC(C)CNC(=O)c1ccc(SCCCl)c(N)c1 | null | null | null |
713,280 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[C:10]2[N:16]=[C:17](S(C)(=O)=O)[N:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[C:9]=2[C:8]1=[O:31].[C:41]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][C... | Cc1ccccc1-c1nc(S(C)(=O)=O)nc2c1C(=O)N(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)CCCN2C | CC(=O)N1CCNCC1 | null | null | null | null | null | null | null | 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 a similar manner to Example 1, 6-[3,5-bis(trifluoromethyl)benzyl]-5,6,7,8,9,10-hexahydro-10-methyl-4-(2-methylphenyl)-2-(methylsulfonyl)-5-oxopyrimido[4,5-b][1,5]diazocine (Compound of Reference Example 21; 88.0 mg) was reacted with 1-acetylpiperazine (23.1 mg) to obtain 9-(4-acetylpiperazine-1-yl)-6-[3,5-bis(triflu... | CC(=O)N1CCN(C2CCN(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(=O)c3c(-c4ccccc4C)ncnc3N2C)CC1 | null | 82.6 | null |
1,350,226 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | S(Br)([Br:3])=O.[Br:5][C:6]1[S:7][CH:8]=[C:9]([CH:11](O)[CH3:12])[N:10]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[S:7][CH:8]=[C:9]([CH:11]([Br:3])[CH3:12])[N:10]=1 | O=S(Br)Br | CC(O)c1csc(Br)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1.5 | To a stirred solution thionyl bromide (0.787 g, 3.78 mmol, 1.05 eq.) in 20 ml dry DCM, cooled to 5° C., was added dropwise a solution of 1-(2-bromo-1,3-thiazol-4-yl)ethanol (0.75 g, 3.60 mmol, 1 eq.) and pyridine (0.285 g, 3.60 mmol, 1 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the react... | CC(Br)c1csc(Br)n1 | null | 92.3 | null |
143,247 | ord_dataset-1895fe091c3f47afa1ee96a41a250de4 | null | 1986-01-01T00:05:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9]O)=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[C:14]([NH2:19])=[CH:15][CH:16]=[CH:17][CH:18]=1.Cl>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:17]2[CH:16]=[CH:15][C:14]([NH2:19])=[C:13]([O:12][CH3:11])[CH:18]=2)=[CH:4][N:3]=1 | COc1ccccc1N | Nc1ncc(CO)c(N)n1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of 6.30 g (0.045 mol) of 2,4-diamino-5-hydroxymethylpyrimidine, 6.15 g (0.05 mol) of o-anisidine and 3.75 ml of concentrated hydrochloric acid in 55 ml of glacial acetic acid was heated to reflux for 6 hours. The mixture was stirred at room temperature overnight. The solvent was removed under vaccum and the ... | COc1cc(Cc2cnc(N)nc2N)ccc1N | null | 70.8 | null |
1,009,842 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1([NH:15][C:16]([C:18]2[CH:19]=[C:20]([F:38])[C:21]([CH3:37])=[C:22]([C:24]3[N:29]=[CH:28][C:27]([C:30]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:26][CH:25]=3)[CH:23]=2)=[O:17])[CH2:14][CH2:13]1>C(Cl)(Cl)Cl.CO>[CH:12]1([NH:15][C:16]([C:18]2[CH:19]=[C:20]([F:38])[C:21]([C... | Cc1c(F)cc(C(=O)NC2CC2)cc1-c1ccc(C(=O)NC(C)(C)C)cn1 | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CO | null | null | null | null | null | null | null | null | null | 60 | null | mCPBA (57-86%, 15 mg) was added to a solution of 6-{5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}-N-(1,1-dimethylethyl)-3-pyridinecarboxamide (Intermediate 9, 20 mg) in chloroform (3 ml) at 60° C. and the reaction maintained at 60° C. for 7 hrs. The reaction was allowed to cool, diluted with methanol, and pas... | Cc1c(F)cc(C(=O)NC2CC2)cc1-c1ccc(C(=O)NC(C)(C)C)c[n+]1[O-] | null | null | null |
522,323 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([O:15][CH2:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([S:28](C)(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[NH3:32]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([O:15][CH2:16][CH2:17][C:18]([... | CC(C)(O)CCOc1c(-c2ccc(S(C)(=O)=O)cc2)cnn(-c2cccc(Cl)c2)c1=O | 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 | null | null | null | The title compound was prepared according to the method of Example 459, substituting 2-(3-chlorophenyl)-4-(3-hydroxy-3-methyl-1-butoxy)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone (Example 475) in place of 2-(3,4-difluorophenyl)-4-(2-hydroxy-2-methyl-1-propoxy)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone. 1H NM... | CC(C)(O)CCOc1c(-c2ccc(S(N)(=O)=O)cc2)cnn(-c2cccc(Cl)c2)c1=O | null | null | null |
1,222,249 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])=[N:8][CH:9]=1)([O-])=O>CO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])=[N:8][CH:9]=1 | COC(=O)c1cccc(Oc2ccc([N+](=O)[O-])cn2)c1 | null | null | [Pd] | 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 | 25 | 6 | To a solution of methyl 3-[(5-nitropyridin-2-yl)oxy]benzoate (14.4 g, 52.5 mmol) in methanol (100 mL) was added palladium carbon (50% water-containing product, 1.40 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 6 hr. The reaction mixture was filtered through celite, and the filtrat... | COC(=O)c1cccc(Oc2ccc(N)cn2)c1 | null | 100.6 | null |
1,302,531 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH:35][CH:36]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:37]([OH:39])=[O:38])[CH3:28].[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48](O)[CH2:47]2>C1COCC1>[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2... | CCc1ccccc1NC(C(=O)O)c1ccccc1 | O[C@H]1CN2CCC1CC2 | null | C(=NC1CCCCC1)=NC1CCCCC1 | Cl | On1nnc2ccccc21 | 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 | PS-DCC (962 mg, 1.37 mmol, loading: 1.33 mmol/g) is suspended in THF (10 mL). HOBT (210 mg, 1.37 mmol), (2-ethyl-phenylamino)-phenyl-acetic acid hydrochloride (I60) (200 mg, 0.68 mmol), and (R)-quinuclidin-3-ol (262 mg, 2.06 mmol) are added and the mixture is shaken at RT overnight. PS-DCC is filtered off and washed wi... | CCc1ccccc1NC(C(=O)O[C@H]1CN2CCC1CC2)c1ccccc1 | null | 21 | null |
1,228,756 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [CH:1]1([N:7]2[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[N:10]([CH3:17])[C:9]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:58]1([NH2:64])[CH2:63][... | NN1CCCCC1 | COc1cc(C(=O)O)ccc1Nc1ncc2c(n1)N(C1CCCCC1)CC(F)(F)C(=O)N2C | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized from 4-(9-cyclohexyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and piperidin-1-amine. The final compound was purified by reverse phase HPLC a... | COc1cc(C(=O)NN2CCCCC2)ccc1Nc1ncc2c(n1)N(C1CCCCC1)CC(F)(F)C(=O)N2C | null | null | null |
1,281,013 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | C(NC(C)C)(C)C.C([Li])CCC.[Li+].CC([N-]C(C)C)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=1.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C>C1COCC1>[F:21][C:22]1[CH:27]=[C:26]([B:29]([OH:34])[OH:30])[C:25]([F:28])=[CH:24][N:23]=1 | Fc1ccc(F)nc1 | CC(C)OB(OC(C)C)OC(C)C | null | CC(C)[N-]C(C)C | [Li+] | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CC(C)NC(C)C | null | null | null | null | null | null | null | null | null | -20 | 4 | Diisopropylamine (1.74 ml, 1.24 g, 12.20 mmol) was dissolved in anhydrous THF (22 ml) and placed under argon. The solution was cooled to −20° C. and then treated with n-butyllithium (7.66 ml, 12.25 mmol, 1.6 M in hexanes) by slow addition over 10 min. The newly formed LDA (LDA= lithium diisopropylamide, this acronyl sh... | OB(O)c1cc(F)ncc1F | null | 44 | null |
373,057 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | [C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH2:11][OH:12])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]=O>FC(F)(F)C(O)=O>[OH:12][CH2:11][CH2:10][C:7]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:19][O:9][CH2:8]1 | OCCC(CO)(c1ccccc1)c1ccccc1 | C=O | 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 | 50 | 2 | In trifluoroacetic acid (50 ml) was dissolved 2,2-diphenyl-1,4-butanediol (5 g) followed by addition of paraformaldehyde (1.7 g) and the mixture was heated and stirred at 50° C. for 2 hours. The reaction mixture was then concentrated under reduced pressure and the residue was dissolved in ethyl acetate, washed with sat... | OCCC1(c2ccccc2)COCc2ccccc21 | null | 85.7 | null |
291,019 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | CCN(CC)CC.[C:8]([O:11][CH2:12][C:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=O)=O)(=[O:10])[CH3:9].[F:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1.Cl>CCO>[C:8]([O:11][CH2:12][C:13]1[N:29]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[N:30]=[C:16]2[C:15]=1[CH2:20][CH2:19][CH2:18][CH... | NNc1ccc(F)cc1 | CC(=O)OCC(=O)C1CCCCC1=O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 4 | Et3N (0.717 mL, 0.520 g, 5.14 mmol) was added to a stirring suspension of 1.00 g (5.04 mmol) of 2-acetoxyacetylcyclohexanone (Dolmazon, R.; Gelin, S. J. Heterocyclic Chem., 1982, 19, 117-121) and 0.820 g (5.04 mmol) of 4-fluorophenylhydrazine·HCl in 20 mL of absolute EtOH. The resulting solution was stirred under N2 fo... | CC(=O)OCc1c2c(nn1-c1ccc(F)cc1)CCCC2 | null | 51.8 | null |
1,729,627 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [Br:1]N1C(=O)CCC1=O.C(#N)C.[CH:12]1([C:18]2[CH:23]=[C:22]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:21]=[C:20]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[Br:1][C:19]1[C:20]([CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)=[CH:21][C:22]([C... | c1c(C2CCCCC2)cc(C2CCCCC2)cc1C1CCCCC1 | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | A 500-mL three-neck flask was charged with 15.7 g of N-bromosuccinimide and 100 g of acetonitrile. Under ice cooling, a dilute solution of 28.4 g of 1,3,5-tricyclohexylbenzene (prepared by known reaction) in 60 g of methylene chloride was added dropwise over 30 minutes. The solution was warmed to room temperature and a... | Brc1c(C2CCCCC2)cc(C2CCCCC2)cc1C1CCCCC1 | null | 81 | null |
1,337,020 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [CH:1]1([CH:6]([N:10]2[CH:14]=[C:13]([C:15]3[C:16]4[CH:23]=[CH:22][N:21](COCC[Si](C)(C)C)[C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[N:11]2)[CH2:7][C:8]#[CH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:1]1([CH:6]([N:10]2[CH:14]=[C:13]([C:15]3[C:16]4[CH:23]=[CH:22][NH:21][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:1... | C#CCC(C1CCCC1)n1cc(-c2ncnc3c2ccn3COCC[Si](C)(C)C)cn1 | 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 | 1 | A solution of 4-[1-(1-cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)-ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (52 mg, 0.12 mmol) in DCM (3 mL) and TFA (1 mL) was stirred for 2 hours. The solvents were removed in vacuo. The resulting residue was dissolved in THF (3 mL) and 6N NaOH (2 mL) was added. Af... | C#CCC(C1CCCC1)n1cc(-c2ncnc3[nH]ccc23)cn1 | null | 81.9 | null |
811,557 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[O:15]1[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16]1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[O:15]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:2]2[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:3]=2)=[CH:16]1 | OCc1ccoc1 | Clc1nc(SCc2ccccc2)ns1 | null | [Cl-] | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 2 | To 2 g of N,N-dimethylformamide, 0.243 g of 5-chloro-3-benzylthio-1,2,4-thiadiazole and 0.098 g of 3-furanmethanol were dissolved, and added 0.045 g of sodium hydride (60% in oil) at about 0° C., followed by stirring at about 0° C. for 1 hour and at room temperature for 2 hours. Then, the reaction mixture was added to ... | c1ccc(CSc2nsc(OCc3ccoc3)n2)cc1 | null | 55.9 | null |
1,673,657 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | C([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]2[C:24]3[C:19](=[CH:20][N:21]=[C:22]4[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:26]=[CH:25][C:23]4=3)[C:18](=[O:36])[CH:17]=[CH:16]2)[CH2:9]1)C1C=CC=CC=1>CO.[C].[Pd]>[CH3:14][C@@H:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[N:1... | C[C@@H]1CCN(Cc2ccccc2)C[C@@H]1n1ccc(=O)c2cnc3c(ccn3COCC[Si](C)(C)C)c21 | null | null | [Pd] | 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 | 5 | rac-1-[(3R,4R)-1-Benzyl-4-methylpiperidin-3-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-h][1,6]naphthyridin-4(7H)-one (98 mg, 0.20 mmol) and 5% palladium-carbon (65 mg) in methanol (2 mL) were stirred at room temperature for 2 hours under a hydrogen atmosphere, then at 40° C. for 5 hours and at room tempera... | C[C@@H]1CCNC[C@@H]1n1ccc(=O)c2cnc3c(ccn3COCC[Si](C)(C)C)c21 | null | 95 | null |
348,762 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | [Cl:1][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13](Cl)=[O:14])[CH:8]=2)[N:3]=1.[BH4-].[Na+].O>O1CCOCC1>[Cl:1][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][OH:14])[CH:8]=2)[N:3]=1 | O=C(Cl)c1ccc2nc(Cl)c(Cl)nc2c1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a suspension of 25.3 g portion of 2,3-dichloroquinoxaline-6-carbonyl chloride synthesized in accordance with the procedure disclosed in JP-A 57-98274 in 400 ml of anhydrous 1,4-dioxane, was added 14.0 g of sodium borohydride, and the mixture was stirred at room temperature for 10 minutes in an atmosphere of nitrogen... | OCc1ccc2nc(Cl)c(Cl)nc2c1 | null | null | null |
1,020,750 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:12]Br.C(OCC)C>O1CCOCC1>[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([Br:12])=[CH:6][C:3]=1[C:4]#[N:5] | COc1ccc(C#N)c(N)c1 | BrBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCOCC | null | null | null | null | null | null | null | null | null | 0 | 1 | 2-Amino-4-methoxybenzonitrile (4.47 g, 30.2 mmol) is dissolved in 70 ml of dioxane and treated at 0° C. with bromine (1.71 ml, 33.2 mmol). It is subsequently stirred at 0° C. for one hour. After addition of diethyl ether, the resulting crystals are filtered off with suction. The desired product is obtained in 81% yield... | COc1cc(N)c(C#N)cc1Br | null | 81 | null |
702,838 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [CH2:1]([N:3]1[CH:7]([CH2:8][CH2:9][O:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[CH:6]=[N:5][NH:4]1)[CH3:2].[C:18]1([C:24]2[O:28][N:27]=[CH:26][C:25]=2[CH2:29][CH2:30][C:31](O)=[O:32])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[CH2:1]([N:3]1[CH:7]([CH2:... | CCN1NN=CC1CCOc1ccc(N)cc1 | O=C(O)CCc1cnoc1-c1ccccc1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | 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 | 8 | A mixture of 4-[2-(3-ethyl-4H-triazol-4-yl)ethoxy]aniline (1.12 g), 3-(5-phenyl-4-isoxazolyl)propionic acid (1.04 g), 1-hydroxy-1H-1,2,3-benzotriazole hydrate (0.89 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.11 g) and N,N-dimethylformamide (20 ml) was stirred at room temperature overnight. The r... | CCN1NN=CC1CCOc1ccc(NC(=O)CCc2cnoc2-c2ccccc2)cc1 | null | 76.2 | null |
1,336,259 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH3:15])[C:12](O)=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:16]1([C:22]2[N:27]=[N:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C([O-])(O)=O.[Na+]>[C:16]1([C:22]2[CH:23]=[CH:24][C:25]3[N:26]([C:12]([CH:11]([C:7]4[CH:6]=[C:5]5[C:10](=[CH:... | CC(C(=O)O)c1ccc2ncccc2c1 | NNc1ccc(-c2ccccc2)nn1 | null | Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 160 | null | To a 2-5 ml Personal Chemistry microwave vial was added 2-(quinolin-6-yl)propanoic acid (0.25 g, 1.2 mmol), 1-(6-phenylpyridazin-3-yl)hydrazine (0.42 g, 2.2 mmol) and conc. HCl (2 mL). The mixture was heated in the microwave at 160° C. for 8 h. After cooling to rt, the mixture was poured into sat. NaHCO3 (100 mL) and t... | CC(c1ccc2ncccc2c1)c1nnc2ccc(-c3ccccc3)nn12 | null | 54.5 | null |
661,265 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | [CH2:1]([N:4]([C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15](B(O)O)=[C:14]([O:23][CH3:24])[CH:13]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH:2]=[CH2:3].[CH3:25][O:26][C:27](=[O:55])[C@H:28]([CH2:40][C:41]1[CH:46]=[CH:45][C:44](OS(C(F)(F)F)(=O)=O)=[CH:43][CH:42]=1)[NH:29][C:30](=[O:39])[C:31]1[C:36]([Cl:37])=... | C=CCN(C(=O)OC(C)(C)C)c1cc(OC)c(B(O)O)c(OC)c1 | COC(=O)[C@H](Cc1ccc(OS(=O)(=O)C(F)(F)F)cc1)NC(=O)c1c(Cl)cccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-(N-Allyl-N-tert-butoxycarbonylamino)-2,6-dimethoxybenzeneboronic acid and N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester were coupled by a similar method as described in Example 7-2) to give N-(2,6-dichlorobenzoyl)-4-[4-(N-allyl-N-tert-butoxycarbonylamino)-2,6-dimethoxyphenyl]-L-phenylal... | C=CCN(C(=O)OC(C)(C)C)c1cc(OC)c(-c2ccc(C[C@H](NC(=O)c3c(Cl)cccc3Cl)C(=O)OC)cc2)c(OC)c1 | null | null | null |
55,998 | ord_dataset-159c363342e44b539e7a5975c873e30d | null | 1979-01-01T00:05:00 | true | [Na].[CH:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([Br:9])[CH:3]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C.C(OCC)C>[Br:9][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2][CH:3]=1 | Oc1ccc(Br)cc1 | CCOC(=O)CBr | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOCC | null | null | null | null | null | null | null | null | null | null | null | 2.76 g of sodium are dissolved in 100 ml of anhydrous ethanol and 20.8 g (0.120 mol) of p-bromophenol are added. 22.1 g (0.132 mol) of ethyl bromoacetate are run into this solution over the course of 20 minutes and the mixture is then heated under reflux for 1 hour. The ethanol is driven off under reduced pressure and ... | CCOC(=O)COc1ccc(Br)cc1 | null | null | null |
433,014 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:36]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:37]([C:40](O)=[O:41])[CH2:38][OH:39].... | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O | N[C@@H](CCC(=O)OCc1ccccc1)C(=O)OCc1ccccc1 | null | CCN=C=NCCCN(C)C | Cc1ccc(S(=O)(=O)O)cc1 | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 20 | To a solution of L-glutamic acid 1,5-dibenzyl ester p-toluenesulfonate (10.0 g), Boc-Ser (4.1 g) and TEA (2.0 g) in DMF (200 ml) are added with stirring WSC (5.0 g) and HOBt (4.0 g) under ice-cooling. The mixture is stirred at room temperature for 20 hours, and thereto is added ethyl acetate (200 ml). The mixture is wa... | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)OCc1ccccc1)C(=O)OCc1ccccc1 | null | 94.3 | null |
1,704,544 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[S:6][C:5]([CH:7]=[C:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]2[CH:32]=[C:31](B3OC(C)(C)C(C)(C)O3)[CH:30]=[C:29]([CH3:42])[CH:28]=2)[N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:42][C:29]1[CH:30... | CCOC(=O)C1CCC(=Cc2ncc(Br)s2)CC1 | Cc1cc(Nc2nccc(C)n2)cc(B2OC(C)(C)C(C)(C)O2)c1 | null | O=C([O-])[O-] | [Na+] | 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 | 80 | null | Ethyl 4-[(5-bromo-1,3-thiazol-2-yl)methylidene]cyclohexanecarboxylate (223 mg, 0.676 mmol), 4-methyl-N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrimidin-2-amine (220 mg, 0.676 mmol) and 1,1′-bis(diphenylphosphino)-ferrocenedichloro palladium(II) dichloromethane complex (49.5 mg, 0.068 mmol) were... | CCOC(=O)C1CCC(=Cc2ncc(-c3cc(C)cc(Nc4nccc(C)n4)c3)s2)CC1 | null | null | null |
698,578 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | [C:1]([C:4]1[N:5]=[C:6]([N:9]2[CH2:12][CH:11](OS(C)(=O)=O)[CH2:10]2)[S:7][CH:8]=1)(=[O:3])[NH2:2].[C:18]([O-:21])(=[S:20])[CH3:19].[K+]>CN(C)C=O>[C:18]([S:20][CH:11]1[CH2:10][N:9]([C:6]2[S:7][CH:8]=[C:4]([C:1](=[O:3])[NH2:2])[N:5]=2)[CH2:12]1)(=[O:21])[CH3:19] | CS(=O)(=O)OC1CN(c2nc(C(N)=O)cs2)C1 | CC([O-])=S | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 80 | 10 | To a solution of 1-(4-carbamoyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (3.04 g, 11.0 mmol) (obtained as described in Reference Example 3(3)) in dimethylformamide (152 ml) was added potassium thioacetate (7.5 g, 65.8 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 10 hours. After ... | CC(=O)SC1CN(c2nc(C(N)=O)cs2)C1 | null | 69.6 | null |
405,891 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | [CH2:1]([O:3][C:4]1[O:5][C@H:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C@H:7]2[N:8]=1)[CH3:2].[NH2:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1C=CC=CC=1>[C:21]([C:20]1[CH:19]=[CH:18][C:17]([NH... | Nc1ccc(C(=O)c2ccccc2)cc1 | CCOC1=N[C@@H]2Cc3ccccc3[C@@H]2O1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | c1ccccc1 | null | null | null | null | null | null | null | null | null | 80 | null | A solution of (±) cis-2-ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (2.50 g, 0.012 mol) in dry toluene (40 ml) was treated with 4-aminobenzophenone (2.43 g, 0.012 mol) and a catalytic amount of p-toluenesulfonic acid (0.25 ml of an anhydrous 0.1M solution of p-toluenesulfonic acid in benzene). The mixture was heated u... | CCOC(=O)N[C@@H]1Cc2ccccc2[C@H]1Nc1ccc(C(=O)c2ccccc2)cc1 | null | 76 | null |
529,716 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21]4[CH2:22][CH2:23][CH2:24][N:25]([CH3:29])[S:26](=[O:28])(=[O:27])[C:20]=4[CH:19]=[CH:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32].C([O-])(=O)C.[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C... | NO | CN1CCCc2c(ccn2CCCN2CCN(c3ccc(F)cc3)CC2)S1(=O)=O | null | CC(=O)[O-] | Cl | [Na+] | 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 | A suspension of 174 mg (0.4 mmol) of Compound 26, 56 mg (0.8 mmol) of hydroxylamine hydrochloride and 66 mg (0.8 mmol) of sodium acetate in 20 ml of methanol was refluxed for 17 hours. Post-treatment and purification were conducted in a similar manner as in Example 20, whereby 119 mg of the title compound were obtained... | CN1CCC(=NO)c2c(ccn2CCCN2CCN(c3ccc(F)cc3)CC2)S1(=O)=O | null | 66.2 | null |
791,061 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | CN(C)C=O.[CH2:6]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=1)[CH2:7][CH2:8][CH3:9].CS(O[CH2:25][CH2:26][C:27]([CH3:31])=[C:28]([F:30])[F:29])(=O)=O.C(=O)([O-])O.[Na+]>O>[CH2:6]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O:17][CH2:25][CH2:26][C:27]([CH3:31])=[C:28]([F:30])[F:29])=[O:16])=[... | CCCCOc1ccc(C(=O)O)cn1 | CC(CCOS(C)(=O)=O)=C(F)F | null | O=C([O-])O | [Na+] | null | 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 | 100 | 3 | To 5 ml of N,N-dimethylformamide were dissolved 0.39 g (2.0 mmol) of 6-butoxynicotinic acid, synthesized by a method in accordance with one used in Intermediate Production Example 1, and 0.40 g (2.0 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate, followed by the addition of 0.34 g (4.0 mmol) of sodium hydrog... | CCCCOc1ccc(C(=O)OCCC(C)=C(F)F)cn1 | null | 75.2 | null |
790,671 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[C:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:6][C:3]=1[C:4]#[N:5].[F:24][C:25]1[CH:26]=[C:27]([OH:32])[CH:28]=[CH:29][C:30]=1[F:31].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=... | Oc1ccc(F)c(F)c1 | N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1Cl | null | O=C([O-])[O-] | [Cs+] | 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 | 100 | 16 | To the product of Example 131 (250 mg, 0.6984 mmol) was added 3,4-difluorophenol (273 mg, 2.095 mmol), Cs2CO3 (683 mg, 2.096 mmol) and toluene (4.5 mL) before heating to 100° C. After stirring 16 hours the reaction solution was filtered and concentrated. The residue was purified by flash chromatography (silica gel) elu... | N#Cc1cc(-c2ccc(Cl)cc2)c(-c2ccccc2Cl)nc1Oc1ccc(F)c(F)c1 | null | null | null |
1,567,124 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][N:16]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Li+].[OH-]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16](... | CCOC(=O)c1cn(COCC[Si](C)(C)C)c2ncnc(-c3cccc([N+](=O)[O-])c3)c12 | null | null | [Li+] | [OH-] | 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 | 60 | 17 | To a solution of ethyl 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (2.00 g, 4.52 mmol) in methanol (5 mL) was added LiOH (500 mg, 20.9 mmol). The resulting solution was stirred for 17 hours at 60° C., concentrated in vacuo, and extracted with ethyl acetate (×3). The ... | C[Si](C)(C)CCOCn1cc(C(=O)O)c2c(-c3cccc([N+](=O)[O-])c3)ncnc21 | null | null | null |
882,022 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:18][CH3:19])=[N:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.CC1C2C(=CC([B:31]3[O:35][C:34]([CH3:37])([CH3:36])[C:33]([CH3:39])([CH3:38])[O:32]3)=CC=2)N=C(C2C=CC=CC=2)N=1>>[CH3:19][O:18][C:6]1[C:5]2[C:10](=[CH:11][C:2]([B:31]3[O:35][C:34]([CH3:37])... | Cc1nc(-c2ccccc2)nc2cc(B3OC(C)(C)C(C)(C)O3)ccc12 | COc1nc(-c2ccccc2)nc2cc(Cl)ccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesized from of 7-chloro-4-methoxy-2-phenylquinazoline (189 mg, 0.7 mmol) as 4-methyl-2-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazoline; off-white solid. MS (ES+): m/z 347.2 (20) MS (ES+): m/z 281.2 (100) [MH+-82]; HPLC: tR=3.19 min (OpenLynx, polar—5 min). | COc1nc(-c2ccccc2)nc2cc(B3OC(C)(C)C(C)(C)O3)ccc12 | null | null | null |
164,536 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@:26](Br)([C@@H:27]([OH:31])[CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:33])[CH:22]=[CH:23]2)[C@@H:18]([CH3:34])[CH2:17]3)[CH2:14][C@@H:13]1[CH3:35])[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].C([SnH](CCCC)CCCC)CCC>>[C:1]([O:4][C@:5... | CC(=O)OCC(=O)[C@@]1(OC(C)=O)[C@@H](C)C[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(Br)[C@@H](O)C[C@@]21C | null | null | CCCC[SnH](CCCC)CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described in Example 1(G), 460 mg of 17α,21-diacetoxy-9α-bromo-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione is debrominated with tributyltin hydride and worked up, thus obtaining 400 mg of 17α,21-diacetoxy-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione, mp 124°-126° C. | CC(=O)OCC(=O)[C@@]1(OC(C)=O)[C@@H](C)C[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C | null | 101.5 | null |
1,009,692 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][C:6]#[N:7])[CH3:2].[NH2:10][OH:11]>CCO>[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][C:6](=[N:10][OH:11])[NH2:7])[CH3:2] | NO | CCN(CC)CCC#N | null | null | 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 | A solution of 3-(diethylamino)propanenitrile (1 g, 8 mmol) and NH2OH (50% in water, 0.73 cm3, 11.9 mmol) in EtOH (10·cm3) were heated to reflux for 24 hours, after which the solvent and excess hydroxylamine were removed by rotary evaporator. The residue was freeze-dried and kept in high vacuum line until it slowly soli... | CCN(CC)CCC(N)=NO | null | 92.6 | null |
1,044,522 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2] | CC(C)(C)OC(=O)N1CCCCC1CN | Clc1cnccn1 | null | null | null | null | null | null | null | 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 (0.18 g) was prepared from (RS) 2-aminomethyl-piperidine-1-carboxylic acid tert butyl ester (0.54 g) and 2-chloropyrazine according to the method of D20. | CC(C)(C)OC(=O)N1CCCCC1CNc1cnccn1 | null | null | null |
992,267 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[I:10]I>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[I:10][C:7]1[C:2]([NH2:1])=[CH:3][CH:4]=[C:5]([O:8][CH3:9])[N:6]=1 | COc1ccc(N)cn1 | II | null | [Ag+2] | O=S(=O)([O-])[O-] | 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 | 25 | 8 | 5-Amino-2-methoxypyridine (10.0 g, 0.081 mol) was dissolved in EtOH (50 mL), and silver sulfate (27.6 g, 0.089 mol) and iodine (22.5 g, 0.089 mol) were added. The reaction was stirred at room temperature overnight, and then the mixture was filtered over Celite to remove solids. The filtrate was concentrated and purifie... | COc1ccc(N)c(I)n1 | null | null | null |
1,489,376 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1/[CH:4]=[N:5]\[OH:6].[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[OH:6]/[N:5]=[C:4](\[Cl:11])/[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[F:1] | O/N=C\c1ccccc1F | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a solution of (E)- and/or (Z)-2-fluoro-benzaldehyde oxime (66.8 g, 480 mmol) in DMF (334 mL) was added N-chlorosuccinimide (29.4 g, 211 mmol) portionwise and after 10 min, keeping the temperature below 50° C., N-chlorosuccinimide (44.1 g, 317 mmol) was added portionwise. The reaction mixture was stirred at room temp... | O/N=C(\Cl)c1ccccc1F | null | 250.9 | null |
305,317 | ord_dataset-180e296d6d6245638d4d22a59120ea01 | null | 1995-01-01T00:02:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([OH:20])[CH2:19][CH2:18][C:13]4([O:17]CCO4)[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[CH3:22]O>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([O:20][CH3:22])[CH2:11][CH2:12][C:13](=[O:17])[CH2:18][CH2:19]3)=[CH:9][C:4]=2[O:3][CH2:2]1 | CO | OC1(c2ccc3c(c2)OCO3)CCC2(CC1)OCCO2 | 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 | A solution of 8-(1,3-Benzodioxol-5-yl)-1,4-dioxa-spiro[4.5]decan8-ol (5.0 g, 1.8 mmole) in 100 mL methanol with 1 mL conc. hydrochloric acid was stirred for 22 hr and the solution concentrated in vacuo. The residue was purified by chromatography on silica eluting with ethyl acetate-hexane (1:19) to give the product (70... | COC1(c2ccc3c(c2)OCO3)CCC(=O)CC1 | null | 70 | null |
1,159,839 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:23](=[S:28])[CH2:24][C:25](=O)[CH3:26])=[O:4].[C:29]([O:33][C:34]([N:36]([CH3:38])[NH2:37])=[O:35])([CH3:32])([CH3:31])[CH3:30]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9]... | CN(N)C(=O)OC(C)(C)C | COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccccc2C(F)(F)F)CN1C(=S)CC(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 | In analogy to the procedure described in example 192 h, (2S,4R)-1-(3-oxo-thiobutyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (example 192 g) was reacted with N-methyl-hydrazinecarboxylic acid tert-butyl ester (CAS Reg. No. 21075-83-2) to give the title compound as off-white sol... | COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccccc2C(F)(F)F)CN1C(=S)CC(C)=NN(C)C(=O)OC(C)(C)C | null | null | null |
373,841 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | [N+:1]([C:4]1[C:5](=[O:12])[NH:6][C:7](=[O:11])[N:8]([CH3:10])[CH:9]=1)([O-:3])=[O:2].Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>O>[C:18]([O:17][C:15](=[O:16])[CH2:14][N:6]1[C:5](=[O:12])[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]([CH3:10])[C:7]1=[O:11])([CH3:21])([CH3:20])[CH3:19] | CC(C)(C)OC(=O)CBr | Cn1cc([N+](=O)[O-])c(=O)[nH]c1=O | 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 | 0.5 | Sodium hydride (0.51 g of a 60% dispersion in mineral oil, 13 mmol) was washed with pentane three times (4 mL each). The compound of Example 109 (2.00 g, 12 mmole) was added portionwise. After the addition was complete, the reaction mixture was stirred for 30 minutes under a nitrogen atmosphere. t-Butyl bromoacetate (1... | Cn1cc([N+](=O)[O-])c(=O)n(CC(=O)OC(C)(C)C)c1=O | null | 57.6 | null |
163,855 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:16])([C:13]([NH2:15])=[O:14])[C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([O:16][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[Cl:17])([C:10... | O=C(Cl)c1ccccc1Cl | NC(=O)C(O)(C(N)=O)c1ccc(Cl)c(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 1 | 26.3 g of 3,4-dichlorophenylhydroxymalonic acid diamide were dissolved in 50 ml of pyridine, and 17.1 g of o-chlorobenzoyl chloride were added at below 30° C. After one hour, the mixture was stirred into cold 1NCl, the precipitate was taken up in ethyl acetate, the mixture was extracted by shaking and the extract was w... | NC(=O)C(OC(=O)c1ccccc1Cl)(C(N)=O)c1ccc(Cl)c(Cl)c1 | null | 33.1 | null |
1,433,346 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | C(N(C(C)C)CC)(C)C.Cl[C:11](Cl)([O:13]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:22][CH2:23][CH:24]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)[OH:25]>C(Cl)Cl>[CH3:32][C:29]1[CH:30]=[CH:31][C:26]([CH:24]2[O:25][C:11](=[O:13])[NH:22][CH2:23]2)=[CH:27][CH:28]=1 | Cc1ccc(C(O)CN)cc1 | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 0 | 1 | Diisopropylethylamine (181 mg, 244 μL, 1.40 mmol) and triphosgene (138 mg, 0.466 mmol) were added successively to a stirred solution of 2-amino-1-(4-methylphenyl)ethanol (35.2 mg, 0.233 mmol) in dry CH2Cl2 (22 mL) at 0° C. under N2. The reaction was stirred at 0° C. for 1 h then concentrated in vacuo to a volume of abo... | Cc1ccc(C2CNC(=O)O2)cc1 | null | null | null |
1,555,308 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]3[CH2:18][CH:19]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:20][CH2:21][C:22]=3[CH:23]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.B.C1COCC1>C1COCC1>[CH2:25]([NH:24][CH:19]1[CH2:18][C:17]2[N:16]=[CH:15][C:14]([NH:13][S:10]([C:7]3[CH:6]=... | CCC(=O)NC1CCc2cc(NS(=O)(=O)c3ccc(OC(F)(F)F)cc3)cnc2C1 | null | null | B | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 6 | To a solution of N-[3-(4-trifluoromethoxy-benzenesulfonylamino)-5,6,7,8-tetrahydroquinolin-7-yl]-propionamide (260 mg, 0.58 mmol) in THF (10 ml) was added dropwise 1M BH3.THF (5.8 ml) and the mixture was stirred at room temperature for 6 h. It was then quenched by careful addition of 1N aqueous HCl (10 ml) and the resu... | CCCNC1CCc2cc(NS(=O)(=O)c3ccc(OC(F)(F)F)cc3)cnc2C1 | null | 64.2 | null |
124,646 | ord_dataset-6d96290c60d941d098c4ddc9d0cb01a0 | null | 1984-01-01T00:12:00 | true | C([S:4][CH2:5][CH:6]1[CH2:17][N:9]2[CH2:10][CH2:11][CH2:12][CH:13]([C:14]([OH:16])=[O:15])[N:8]2[C:7]1=[O:18])(=O)C.P([O-])([O-])(O)=O.[Na+].[Na+]>Cl>[SH:4][CH2:5][CH:6]1[CH2:17][N:9]2[CH2:10][CH2:11][CH2:12][CH:13]([C:14]([OH:16])=[O:15])[N:8]2[C:7]1=[O:18] | CC(=O)SCC1CN2CCCC(C(=O)O)N2C1=O | null | null | Cl | O=P([O-])([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1.8 g of 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid were heated at 95° C. for 1.5 hours in 2 M hydrochloric acid. The mixture was cooled, the pH was adjusted to 3 by the addition of disodium hydrogen orthophosphate and the aqueous solution was extracted repeatedly with ethyl aceta... | O=C(O)C1CCCN2CC(CS)C(=O)N12 | null | 72.3 | null |
1,642,159 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][C:26]([CH3:28])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:25][CH:26]([N:22]1[CH2:23][CH2:24][CH:19]([N:14]2[CH:1... | CC(C)=O | O=c1ccn(C2CCNCC2)nc1-c1ccnn1-c1ccccc1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 8 | 3-(1-Phenyl-1H-pyrazol-5-yl)-1-piperidin-4-ylpyridazin-4(1H)-one (0.20 g), acetone (0.23 mL) and acetic acid (1.0 mL) were dissolved in THF (10 mL), sodium triacetoxyborohydride (0.66 g) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, a... | CC(C)N1CCC(n2ccc(=O)c(-c3ccnn3-c3ccccc3)n2)CC1 | null | null | null |
157,944 | ord_dataset-58ec6779628e43e2b3f0972725f262e6 | null | 1987-01-01T00:05:00 | true | [Na].[CH2:2]([SH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:14][CH:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:12]=1[CH:27]=[O:28]>CO>[CH2:2]([S:9][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:14][CH:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:2... | SCc1ccccc1 | O=CC1=C(Cl)c2ccccc2OC1c1ccccc1 | null | [Na] | 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 | 0.25 | 1.25 g sodium is allowed to react with 150 ml absolute methanol. When all the sodium has disappeared, one adds 6 ml benzylmercaptan and 13.5 g 4-chloro-3-formyl-flav-3-ene and refluxes over 15 minutes. After solvent evaporation and extraction with methylene chloride the residue is crystallized in a mixture of hexane an... | O=CC1=C(SCc2ccccc2)c2ccccc2OC1c1ccccc1 | null | null | null |
1,671,285 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C>S(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10] | COc1cc(CC(=O)O)ccc1[N+](=O)[O-] | C1CCNC1 | 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 | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of the product of EXAMPLE 30B (1 g, 4.74 mmol) in thionyl dichloride (20 mL) was stirred at reflux for 3 hours. The solution was concentrated and the residue was diluted with dry dichloromethane (20 mL) and dropped into a solution of pyrrolidine (0.63 mL, 7.1 mmol) and diisopropyl ethylamine (1.7 mL, 9.5 mmo... | COc1cc(CC(=O)N2CCCC2)ccc1[N+](=O)[O-] | null | null | null |
394,501 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [CH2:1]([N:3]1[C:11]2[N:10]=[CH:9][NH:8][C:7]=2[C:6](=[O:12])[NH:5][C:4]1=[O:13])[CH3:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:14]([N:8]1[C:7]2[C:6](=[O:12])[NH:5][C:4](=[O:13])[N:3]([CH2:1][CH3:2])[C:11]=2[N:10]=[CH:9]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=... | BrCc1ccccc1 | CCn1c(=O)[nH]c(=O)c2[nH]cnc21 | null | O=C([O-])[O-] | [K+] | 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 | 18 g (0.1 mol) of 3-ethylxanthine were stirred at 60° C. for 2 hours with 19.2 g (0.11 mol) of benzyl bromide and 15.2 g (0.11 mol) of potassium carbonate. The reaction solution was transferred to an Edenmeyer flask and treated with 1000 ml of water. The precipitate was filtered off with suction, washed several times w... | CCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1 | null | null | null |
1,320,451 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | Cl.Cl[CH2:3][C:4]1[N:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.N1(O)C2C=CC=CC=2N=N1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=1>>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]2[N:8]([C:4]([CH2:3][O:37][C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3... | Oc1cccnc1 | Cc1ccc(-c2nc3ccc(C)cn3c2CCl)cc1 | null | Cl | On1nnc2ccccc21 | null | null | null | null | 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 Method A and the experimentals described for compound 139 from 3-(chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride and 1H-benzo[d][1,2,3]triazol-1-ol. and pyridin-3-ol. m/e+ 350 for C21H20N3O [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 8.38 (d, J=1.8 Hz, 1H), 8.27 ... | Cc1ccc(-c2nc3ccc(C)cn3c2COc2cccnc2)cc1 | null | null | null |
1,595,390 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[CH2:13]([O:15][CH:16]([O:22]CC)[C:17](OCC)=O)C>C[N+]([O-])=O>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]2[C:5](=[CH:6][CH:7]=1)[CH:17]([C:16]([O:15][CH3:13])=[O:22])[O:10][CH2:9][CH2:8]2 | COc1c(Br)cccc1CCO | CCOC(=O)C(OCC)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | 0 | 0.17 | 2-(3-bromo-2-methoxyphenypethanol To a solution of methyl (3-bromo-2-methoxyphenyl)acetate (8.2 g, 31.66 mmol) in 200 mL of dry THF under N2 at room temperature was added LiBH4 (32 mL, 63.32 mmol, 2M THF). After 1.5 hours, the reaction was warmed to reflux for 3 hours, and then cooled to room temperature. The solution ... | COC(=O)C1OCCc2c1ccc(Br)c2OC | null | null | null |
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