Triethylamine → HCID 14208199, compound

HRID 620570Notes

Reaction equation

HRID 620570 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[NH:4][C:3]1=[O:19].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:29](O)=[O:30])=[CH:21]1.C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C>CN(C=O)C>[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:29]([NH:1][CH:2]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=3[NH:4][C:3]2=[O:19])=[O:30])=[CH:21]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 69867Indole-3-Carboxylic AcidHCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 14208199HCID 14208199, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(RS)-Amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (49.2 mg, 0.196 mmol), indole-3-carboxylic acid (37.9 mg, 0.235 mmol) and 1M DCC in CH2C2 solution (0.235 ml, 0.235 mmol) were mixed in DMF (2 ml) and the pH adjusted to 9.0 with triethylamine (32.7 μl, 0.235 mmol). The reaction was stirred 18 hrs. at 25° C., the DMF removed in vacuo, and the residue chromatographed on a Waters Semi-Prep C-18 30×0.9 cm column (gradient elution of 5 to 95% CH3CN in H2O) to give the title compound as a white solid from MeOH/ether: (m.p. 265°-268°).

Workup

  1. customat 25° C., the DMF removed in vacuo
  2. customthe residue chromatographed on a Waters Semi-Prep C-18 30×0.9 cm column (gradient elution of 5 to 95% CH3CN in H2O)

Sources & evidence

ORD record
ord-b0e1309411514c18921d0f907c9e371a
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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