Dimethylamine → ((S)-5-dimethylcarbamoyl-5-(2-{[1-methyl-2-(6-trifluoromethyl-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-acetylamino)-pentyl]-carbamic acid tert-butyl ester

HRID 411068Notes

Reaction equation

HRID 411068 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:17][C:18](=[O:47])[CH2:19][NH:20][C:21]([C:23]1[CH:46]=[CH:45][C:26]2[N:27]([CH3:44])[C:28]([NH:30][C:31]3[S:32][C:33]4[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:34]=4[N:35]=3)=[N:29][C:25]=2[CH:24]=1)=[O:22])[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:48][NH:49][CH3:50].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]([C:14](=[O:15])[N:49]([CH3:50])[CH3:48])[NH:17][C:18](=[O:47])[CH2:19][NH:20][C:21]([C:23]1[CH:46]=[CH:45][C:26]2[N:27]([CH3:44])[C:28]([NH:30][C:31]3[S:32][C:33]4[CH:39]=[C:38]([C:40]([F:43])([F:41])[F:42])[CH:37]=[CH:36][C:34]=4[N:35]=3)=[N:29][C:25]=2[CH:24]=1)=[O:22])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86656981(S)-6-tert-Butoxycarbonylamino-2-(2-{[1-methyl-2-(6-trifluoromethyl-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-acetylamino)-hexanoic acid

Product 1

HCID 86656982((S)-5-dimethylcarbamoyl-5-(2-{[1-methyl-2-(6-trifluoromethyl-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-acetylamino)-pentyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

[(S)-5-Dimethylcarbamoyl-5-(2-{[1-methyl-2-(6-trifluoromethyl-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-acetylamino)-pentyl]-carbamic acid tert-butyl ester (200 mg) was prepared by following General Procedure F starting from (S)-6-tert-butoxycarbonylamino-2-(2-{[1-methyl-2-(6-trifluoromethyl-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-acetylamino)-hexanoic acid (260 mg), 2 M dimethylamine in THF (1 mL), HBTU (400 mg), and DIEA (400 uL) in DMF (2 mL).

Sources & evidence

ORD record
ord-0c5363599f534d2f88683412cd5276b1
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

Loading…