Triethylamine → (RS)-N-(2,3-Dihydro-1-(2-hydroxyethyl)-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide

HRID 1110202Notes

Reaction equation

HRID 1110202 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][CH2:20][OH:21])[C:3]1=[O:22].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1[C:32](Cl)=[O:33].C(N(CC)CC)C>C(Cl)Cl>[OH:21][CH2:20][CH2:19][N:4]1[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:8][CH:2]([NH:1][C:32]([C:24]2[NH:23][C:31]3[C:26]([CH:25]=2)=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:33])[C:3]1=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103571453-(RS)-Amino-1,3-dihydro-1-(2-hydroxyethyl)-5-phenyl-2H-1,4-benzodiazepin-2-oneHCID 118162081H-indole-2-carbonyl Chloride

Product 1

HCID 14800306(RS)-N-(2,3-Dihydro-1-(2-hydroxyethyl)-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(RS)-Amino-1,3-dihydro-1-(2-hydroxyethyl)-5-phenyl-2H-1,4-benzodiazepin-2-one (69.0 mg, 0.234 mmole), indole-2-carbonyl chloride (43.1 mg, 0.240 mmole) and triethylamine (33.3 μl, 0.240 mmole) were combined in CH2Cl2 (3 ml). The reaction was stirred for 10 minutes at room temperature then chromatographed on silica gel (14% acetone in CH2Cl2). The product fractions were combined and evaporated to dryness in vacuo. The residue was triturated with Et2O to yield the title compound: (m.p. 160°-171° C.).

Workup

  1. customthen chromatographed on silica gel (14% acetone in CH2Cl2)
  2. customevaporated to dryness in vacuo
  3. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-b93e0f6143c549ad880e2ec3ba37dacd
Source dataset
uspto-grants-1994_06
Patent number
US05324726

Reaction notes

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