Hydrazine → HCID 178508272, compound

HRID 2367532Notes

Reaction equation

HRID 2367532 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][CH:25]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:34])[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][CH:25]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:34])[N:27]=3)[CH2:18]2)[N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178509577HCID 178509577, compound

Product 1

HCID 178508272HCID 178508272, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-(2-amino-6-{2-[4-(2-chlorophenyl)-1H-imidazol-2-yl]-4-morpholinyl}-4-pyrimidinyl)-2-fluorobenzonitrile (50 mg, 0.105 mmol) and hydrazine (0.167 mL, 5.25 mmol) in ethanol (2 mL) was heated at 120° C. under microwave conditions with stirring for 1 hour. The reaction mixture was filtered and concentrated, and the resulting residue dried in vacuo to afford the title compound (40 mg) as a yellow solid. LC-MS (ES) m/z=488 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.10-3.16 (m, 1H), 3.22-3.28 (m, 1H), 3.71-3.76 (m, 1H), 4.04-4.07 (m, 1H), 4.30-4.34 (m, 1H), 4.65-4.68 (m, 1H), 4.73 (m, 1H), 5.38 (s, 2H), 6.20 (s, 2H), 6.71 (s, 1H), 7.21-7.25 (m, 1H), 7.33-7.37 (m, 1H), 7.46-7.48 (m, 1H), 7.60-7.63 (m, 1H), 7.69-7.73 (m, 2H), 7.99 (s, 1H), 8.11-8.13 (m, 1H), 11.52 (s, 1H), 12.53 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customthe resulting residue dried in vacuo

Sources & evidence

ORD record
ord-66732a1f4f894b4d9f6399a498fd8dcb
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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