Diethyl Ether → HCID 14208239, compound

HRID 620574Notes

Reaction equation

HRID 620574 reaction equation
Cl[CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3]1=[O:20].[NH2:21][CH2:22][C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2.CCOCC>COCCOC>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3](=[O:20])[CH:2]([NH:21][CH2:22][C:23]2[NH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 582331(1h-indol-2-ylmethyl)amineHCID 15167810HCID 15167810, compound

Product 1

HCID 14208239HCID 14208239, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
25 °C

Procedure

3-(RS)-Chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one (150 mg, 0.520 mmol) and 2-aminomethylindole (75.9 mg, 0.520 mmol) were combined in 1,2-dimethoxyethane (3 ml) and the mixture stirred 20 min. at 25° C. The mixture was evaporated to dryness in vacuo and the residue treated with H2O and extracted with EtOAc (3x). The combined extracts were washed with H2O (1X), dried over MgSO4, filtered and stripped to dryness in vacuo to give an orange oil which, after chromatography on silica gel (4% MeOH in CH2Cl2) provided the title compound as a white solid from ether: (m.p. 200°-202°).

Workup

  1. customThe mixture was evaporated to dryness in vacuo
  2. additionthe residue treated with H2O
  3. extractionextracted with EtOAc (3x)
  4. washThe combined extracts were washed with H2O (1X)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customto give an orange oil which

Sources & evidence

ORD record
ord-0bca338837ef4df09d2f63a938cd4b42
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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