Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 22224913, compound

HRID 1745790Notes

Reaction equation

HRID 1745790 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:29]=[CH:28][C:11]3[N:12]=[C:13]([C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=4)[C:21]([NH:23][NH2:24])=[O:22])[CH2:14][C:15](=[O:17])[NH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.Cl.[C:31](=N)(OCC)[CH3:32]>N1C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:29]=[CH:28][C:11]3[N:12]=[C:13]([C:18]4[CH:27]=[CH:26][CH:25]=[C:20]([C:21]5[O:22][C:31]([CH3:32])=[N:24][N:23]=5)[CH:19]=4)[CH2:14][C:15](=[O:17])[NH:16][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 69592775HCID 69592775, compound

Product 1

HCID 22224913HCID 22224913, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-[7-(4-fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzoic acid hydrazide (Starting material 8a-2) (58 mg, 0.15 mmol) and ethyl acetimidate hydrochloride (74 mg, 0.6 mmol) in pyridine (0.6 mL) was heated to 100° C. for 2 h. The mixture was cooled to 23° C., diluted with H2O (30 mL) and stirred for 20 min. The precipitate was collected by filtration, and the crude product was purified by chromatography on silica gel using ethyl acetate/hexane (2:1) as eluent. The purified product was crystallized from Et2O/hexane to give the title compound as light yellow solid (28 mg).

Workup

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

Sources & evidence

ORD record
ord-9d5c42ea890d4b3199b9d2b6adf8c616
Source dataset
uspto-grants-2006_03
Patent number
US07018998B2

Reaction notes

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