Water → (2R)-4-benzyl-2-hydroxymethyl-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxamide

HRID 1633861Notes

Reaction equation

HRID 1633861 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([C:19]([O:21]C(C)(C)C)=O)[CH:17]=[CH:18][C:12]=2[NH:11][C@H:10]([CH2:26][OH:27])[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[C:31]1[CH2:39][NH:40][CH3:41].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>>[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([C:19]([N:40]([CH3:41])[CH2:39][C:31]3[N:30]([CH3:29])[C:38]4[C:33]([CH:32]=3)=[CH:34][CH:35]=[CH:36][CH:37]=4)=[O:21])[CH:17]=[CH:18][C:12]=2[NH:11][C@H:10]([CH2:26][OH:27])[C:9]1=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 6

HCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 54251532Tert-butyl (2R)-4-benzyl-2-hydroxymethyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate

Product 1

HCID 54319432(2R)-4-benzyl-2-hydroxymethyl-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxamideYield 83%

Procedure

According to the procedure of Example 8, except using tert-butyl (2R)-4-benzyl-2-hydroxymethyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate (0.39 g, 1.0 mmole), 1-methyl-2-(methylaminomethyl)indole (0.18 g, 1.1 mmole), Et3N (0.31 mL, 2.2 mmole), HOBt.H2O (0.15 g, 1.1 mmole), and EDC.HCl (0.21 g, 1.1 mmole), the title compound (0.40 g, 83%) was prepared as an off-white solid following flash chromatography on silica gel (gradient: 1-3% MeOH/CHCl3): MS (ES) m/e 483.2 (M+H)+.

Sources & evidence

ORD record
ord-8e2097510c364f5ab6c98275205bcc92
Source dataset
uspto-grants-2003_01
Patent number
US06503903B1

Reaction notes

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