Diethyl Ether → HCID 14208239, compound

HRID 1084540Notes

Reaction equation

HRID 1084540 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 (3×). The combined extracts were washed with H2O (1×), 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 (3×)
  4. washThe combined extracts were washed with H2O (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customto give an orange oil which

Sources & evidence

ORD record
ord-7544138f09764fd7830c507f6fe856c2
Source dataset
uspto-grants-1991_04
Patent number
US05004741

Reaction notes

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