(2R)-2-[(carbomethoxy)methyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylic acid → (2R)-N,4-dimethyl-N-[[1-(4-hydroxybenzyl)-1H-indol-2-yl]methyl]-2-(hydroxymethyl)-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxamide

HRID 1884537Notes

Reaction equation

HRID 1884537 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:16][NH:17][CH3:18])=[CH:4][CH:3]=1.CN1C2C(=CC=CC=2)C=C1CNC.[OH:34][CH2:35][C@@H:36]1[C:42](=[O:43])[N:41]([CH3:44])[CH2:40][C:39]2[CH:45]=[C:46]([C:49](O)=[O:50])[CH:47]=[CH:48][C:38]=2[NH:37]1.C(C[C@@H]1C(=O)N(C)CC2C=C(C(O)=O)C=CC=2N1)(OC)=O>>[CH3:18][N:17]([CH2:16][C:8]1[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:20][CH:19]=2)[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:49]([C:46]1[CH:47]=[CH:48][C:38]2[NH:37][C@H:36]([CH2:35][OH:34])[C:42](=[O:43])[N:41]([CH3:44])[CH2:40][C:39]=2[CH:45]=1)=[O:50]

Participants

5

Reactant 4

HCID 11220043(2R)-2-[(carbomethoxy)methyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylic acidHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 235055811-(4-Hydroxybenzyl)-2-(methylaminomethyl)indoleHCID 53726847(2R)-2-(hydroxymethyl)-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylic acid

Product 1

HCID 54280820(2R)-N,4-dimethyl-N-[[1-(4-hydroxybenzyl)-1H-indol-2-yl]methyl]-2-(hydroxymethyl)-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxamideYield 92.2%

Procedure

According to the procedure of Example 1 (a), except substituting 1-(4-hydroxybenzyl)-2-(methylaminomethyl)indole (0.40 g, 1.50 mmole) for the 1-methyl-2-(methylaminomethyl)indole, and substituting (2R)-2-(hydroxymethyl)-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylic acid (0.34 g, 1.37 mmole) for the (2R)-2-[(carbomethoxy)methyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylic acid, the title compound (0.63 g, 92%) was prepared as an off-white solid: MS (ES) m/e 499 (M+H)+.

Sources & evidence

ORD record
ord-ca667d9ab3a34c53a1204a25cda10480
Source dataset
uspto-grants-2004_07
Patent number
US06765005B2

Reaction notes

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