Triethylamine → 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(3-thiophene carbonylamino)-2H-1,4-benzodiazepin-2-one

HRID 1084533

Reaction equation

HRID 1084533 reaction equation
[NH2:1][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].[S:21]1[CH:25]=[CH:24][C:23]([C:26](Cl)=[O:27])=[CH:22]1.C(N(CC)CC)C>C(Cl)Cl>[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:1][C:26]([C:23]2[CH:24]=[CH:25][S:21][CH:22]=2)=[O:27])[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27763773-Thenoyl chlorideHCID 156371501,3-dihydro-5-(2-fluorophenyl)-3-amino-2H-1,4-benzodiazepin-2-one

Product 1

HCID 142082171,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(3-thiophene carbonylamino)-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

3-(RS)-Amino-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one (75 mg, 0.229 mmol), thiophene-3-carbonyl chloride (44.9 mg, 0.306 mmol) and triethylamine (42.5 μl, 0.306 mmol) were combined in CH2Cl2 (4 ml) and stirred 10 min. at 25° C. The reaction was concentrated and chromatographed on silica gel (2% MeOH in CH2Cl2) to give the title compound as a white solid from Et2O: (m.p. 238°-239°).

Workup

  1. concentrationThe reaction was concentrated
  2. customchromatographed on silica gel (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-12c286210b2545c19ed77ba8d8b3186e
Source dataset
uspto-grants-1991_04
Patent number
US05004741

Linked notes

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