Hydrazine hydrate (1:1) → HCID 69592775, compound

HRID 859609Notes

Reaction equation

HRID 859609 reaction equation
C(O[C:5](=[O:33])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH2:13][C:14](=[O:32])[NH:15][C:16]3[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27]C=[C:25]([CH2:29][F:30])[CH:24]=4)[C:20](C)=[CH:19][C:17]=3[N:18]=2)[CH:7]=1)C=C.O.[NH2:35][NH2:36]>CO.O>[F:30][C:29]1[CH:27]=[CH:28][C:23]([C:21]2[CH:20]=[CH:19][C:17]3[N:18]=[C:12]([C:8]4[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=4)[C:5]([NH:35][NH2:36])=[O:33])[CH2:13][C:14](=[O:32])[NH:15][C:16]=3[CH:22]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69592802HCID 69592802, compound

Product 1

HCID 69592775HCID 69592775, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 3-[7-(3-fluoromethyl-phenyl)-8-methyl-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzoic acid allyl ester (Starting material 8a-1) (207 mg, 0.5 mmol) in MeOH (3.5 mL) was added hydrazine hydrate (0.25 mL, 5 mmol). The mixture was stirred at 60° C. for 15 h, then cooled to 23° C. and diluted with H2O (35 mL). The precipitate was collected by filtration and dried, and the crude product was purified by chromatography on silica gel using ethyl acetate/hexane (1:1) as eluent. The purified product was crystallized from Et2O/hexane to give the title compound as light yellow solid (64 mg).

Workup

  1. temperaturecooled to 23° C.
  2. filtrationThe precipitate was collected by filtration
  3. customdried
  4. customthe crude product was purified by chromatography on silica gel
  5. customThe purified product was crystallized from Et2O/hexane

Sources & evidence

ORD record
ord-abd516e2903c44c399e10fcc19dd2bec
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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