Triethylamine → HCID 10001488, compound

HRID 1084529Notes

Reaction equation

HRID 1084529 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].C([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])C>C(Cl)Cl>[NH:22]1[C:23]2[C:24](=[CH:18][CH:5]=[CH:6][CH:7]=2)[C:26]([CH2:2][C:3]([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:19])=[CH:25]1

Participants

4

Reactant 2

HCID 8471Triethylamine2×HCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 10001488HCID 10001488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(RS)-Amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (75 mg, 0.298 mmol) and indole-3-acetyl chloride (57.8 mg, 0.298 mmol) were combined in CH2Cl2 (2 ml) and the pH adjusted to 9.0 with triethylamine (TEA) 41 μl, 0.298 mmol). After stirring 15 min., a second portion of indole-3-acetyl chloride (44 mg, 0.175 mmol) and TEA (30 μl, 0.215 mmol) were added and the reaction stirred an additional 15 min. The completed reaction was diluted with CH2Cl2, washed with H2O (1X) and brine (1X), dried over MgSO4, filtered and stripped to dryness in vacuo. The residue was chromatographed on silica gel (5% MeOH in CH2Cl2) to give the title compound as a pinkish solid from Et2O: (m.p. 264°-265°).

Workup

  1. stirringthe reaction stirred an additional 15 min
  2. customThe completed reaction
  3. washwashed with H2O (1X) and brine (1X)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe residue was chromatographed on silica gel (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-8c4fcf40a378444ab0fc73a1dfeaf8cd
Source dataset
uspto-grants-1991_04
Patent number
US05004741

Reaction notes

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