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

HRID 1884536Notes

Reaction equation

HRID 1884536 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.[CH3:34][C@@H:35]1[C:41](=[O:42])[N:40]([CH3:43])[CH2:39][C:38]2[CH:44]=[C:45]([C:48]([OH:50])=O)[CH:46]=[CH:47][C:37]=2[NH:36]1.C(C[C@@H]1C(=O)N(C)CC2C=C(C(O)=O)C=CC=2N1)(OC)=O>>[OH:1][C:2]1[CH:3]=[CH:4][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][N:17]([CH3:18])[C:48]([C:45]2[CH:46]=[CH:47][C:37]3[NH:36][C@H:35]([CH3:34])[C:41](=[O:42])[N:40]([CH3:43])[CH2:39][C:38]=3[CH:44]=2)=[O:50])=[CH:19][CH:20]=1

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 18346792HCID 18346792, compoundHCID 235055811-(4-Hydroxybenzyl)-2-(methylaminomethyl)indole

Product 1

HCID 54191214(2R)-N-[[1-(4-hydroxybenzyl)-1H-indol-2-yl]methyl]-3-oxo-N,2,4-trimethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxamideYield 90%

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)-2,4-dimethyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylic acid (0.32 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 (0.59 g, 90%) was prepared as an off-white solid: MS (ES) m/e 483 (M+H)+.

Sources & evidence

ORD record
ord-999be130ed32473dacc10ea0430bbfaa
Source dataset
uspto-grants-2004_07
Patent number
US06765005B2

Reaction notes

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