Hydrazine → HCID 178432616, compound

HRID 2367403Notes

Reaction equation

HRID 2367403 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[NH:24][C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:26]([CH3:28])[N:27]=3)[CH2:18]2)[N:3]=1.[NH2:35][NH2:36]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:11]([C:12]([NH2:13])=[N:35][NH:36]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[NH:24][C:25]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[C:26]([CH3:28])[N:27]=3)[CH2:18]2)[N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178432617HCID 178432617, compound

Product 1

HCID 178432616HCID 178432616, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-{2-amino-6-[2-(4-methyl-5-phenyl-1H-imidazol-2-yl)-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (100 mg, 0.220 mmol) and hydrazine (0.348 mL, 10.98 mmol) in ethanol (2 mL) was heated under microwave conditions with stirring for 1 hour. The mixture was concentrated, and the crude product was purified by RPHPLC to afford the title compound (90 mg) as a pale yellow solid. LC-MS (ES) m/z=468 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 2.35 (s, 3H), 3.04-3.22 (m, 2H), 3.66-3.75 (m, 1H), 4.04 (d, J=11.2 Hz, 1H), 4.32 (d, J=12.8 Hz, 1H), 4.52-4.58 (m, 1H), 4.70 (s, 1H), 5.38 (s, 2H), 6.20 (s, 2H), 6.70 (s, 1H), 7.17-7.28 (m, 1H), 7.34-7.46 (m, 2H), 7.52-7.66 (m, 3H), 7.71 (d, J=8.4 Hz, 1H), 7.96 (s, 1H), 11.52 (s, 1H), 12.20 (s, 1H).

Workup

  1. temperaturewas heated under microwave conditions
  2. concentrationThe mixture was concentrated
  3. customthe crude product was purified by RPHPLC

Sources & evidence

ORD record
ord-862983538e604d45af7ec1838eea133a
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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