Water → HCID 178508274, compound

HRID 2367362Notes

Reaction equation

HRID 2367362 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[CH:19]([C:23]3[NH:24][CH:25]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=4)[N:27]=3)[CH2:18]2)[N:3]=1.[NH2:35][NH2:36].CC#N.[OH2:40]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[C:14]3[C:11]([C:12]([NH2:13])=[N:35][NH:36]3)=[CH:10][CH:9]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:40][CH:19]([C:23]3[NH:24][CH:25]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=4)[N:27]=3)[CH2:18]2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 9321HydrazineHCID 178509579HCID 178509579, compound

Product 1

HCID 178508274HCID 178508274, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(2-amino-6-{2-[4-(3-chlorophenyl)-1H-imidazol-2-yl]-4-morpholinyl}-4-pyrimidinyl)-2-fluorobenzonitrile (310 mg, 0.651 mmol) and hydrazine (1.03 mL, 32.6 mmol) in ethanol (4 mL) was heated under microwave conditions with stirring for 1 hour. The mixture was concentrated, and the resulting residue was purified by Prep-HPLC using CH3CN in water (10 mmol ammonium hydrogen carbonate in water) from 40% to 60% in 9 minutes to afford the title compound (96 mg) as a yellow solid. LC-MS (ES) m/z=488 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.07-3.15 (m, 1H), 3.17-3.23 (m, 1H), 3.69-3.75 (m, 1H), 4.04-4.06 (m, 1H), 4.30-4.34 (m, 1H), 4.60-4.64 (m, 1H), 4.72-4.75 (m, 1H), 5.38 (s, 2H), 6.20 (s, 2H), 6.71 (s, 1H), 7.21-7.30 (m, 1H), 7.34-7.47 (m, 1H), 7.60-7.63 (m, 1H), 7.69-7.72 (m, 1H), 7.74-7.76 (m, 2H), 7.83-7.85 (m, 1H), 7.99 (s, 1H), 11.52 (s, 1H), 12.43-12.70 (m, 1H).

Workup

  1. temperaturewas heated under microwave conditions
  2. concentrationThe mixture was concentrated
  3. customthe resulting residue was purified by Prep-HPLC
  4. customin 9 minutes

Sources & evidence

ORD record
ord-49e2985224d148f7851b72c0586060c6
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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