Water → HCID 135487666, compound

HRID 2298785Notes

Reaction equation

HRID 2298785 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:14]=[C:13]([C:15]2[CH:34]=[CH:33][C:18]3[NH:19][CH:20]([CH2:28][C:29]([O:31]C)=[O:30])[C:21](=[O:27])[N:22]([CH:24]4[CH2:26][CH2:25]4)[CH2:23][C:17]=3[CH:16]=2)[O:12][N:11]=1.O.[Li+].[OH-]>COCCOC>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]1[N:14]=[C:13]([C:15]2[CH:34]=[CH:33][C:18]3[NH:19][CH:20]([CH2:28][C:29]([OH:31])=[O:30])[C:21](=[O:27])[N:22]([CH:24]4[CH2:25][CH2:26]4)[CH2:23][C:17]=3[CH:16]=2)[O:12][N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 135528934HCID 135528934, compound

Product 1

HCID 135487666HCID 135487666, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

130 mg of methyl 7-[3-(1H-benzimidazol-2-yl)-[1,2,4]oxadiazol-5-yl]-4-cyclopropyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine-2-acetate are hydrolyzed in 4 ml of ethylene glycol dimethyl ether and 3 ml of water and also 90 mg of LiOH analogously to Preparation Example 2. 80 mg are obtained as a colorless solid. 1H NMR (400 MHz, DMSO): 0.59 (m, 1H), 0.77 (m, 1H), 2.58 (1 H, dd, J=5.2 Hz, 16.7 Hz) 2.75-2.85 (m, 2H), 2.96 (s, 3H), 4.09 (d, 1H, 16.9 Hz), 5.13 (m, 1H), 5.47 (d, 1H, 16.9 Hz), 6.76 (d, 1H, 8.6 Hz), 6.92 (m, 1H), 7.25-7.90 (m, 6H), 12.5 (broad s, 1H), 13.52 (m, 1H).

Workup

  1. custom80 mg are obtained as a colorless solid

Sources & evidence

ORD record
ord-6d374cfcbf41429eb4ace9ea673634ba
Source dataset
uspto-grants-2002_12
Patent number
US06495545B1

Reaction notes

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