Hydrazine hydrate (1:1) → HCID 178508269, compound

HRID 2367408Notes

Reaction equation

HRID 2367408 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:27][C:26]4[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:25]=4[N:24]=3)[CH2:18]2)[N:3]=1.[OH2:33].[NH2:34][NH2:35]>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:34][NH:35]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:33][CH:19]([C:23]3[NH:27][C:26]4[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:25]=4[N:24]=3)[CH2:18]2)[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178509574HCID 178509574, compound

Product 1

HCID 178508269HCID 178508269, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-{2-amino-6-[2-(5-chloro-1H-benzimidazol-2-yl)-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (140 mg, 0.311 mmol) in ethanol (5 mL) stirred at room temperature was added hydrazine hydrate (156 mg, 3.11 mmol), and the reaction mixture was stirred overnight at 85° C. The solvent was evaporated in vacuo to give the crude product. The crude product was added to a silica gel column and was eluted with CH2Cl2/MeOH to afford the title compound (41 mg) as a yellow solid. LC-MS (ES) m/z=462 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.13-3.17 (m, 2H), 3.81 (t, J=13.2 Hz, 1H), 4.12 (d, J=9.6 Hz, 1H), 4.35 (d, J=9.6 Hz, 1H), 4.84-4.89 (m, 2H), 5.40 (s, 2H), 6.30 (s, 2H), 6.72 (s, 1H), 7.22 (t, J=9.6 Hz, 1H), 7.48-7.50 (m, 1H), 7.60-7.73 (m, 3H), 7.97 (s, 1H), 11.55 (s, 1H), 12.80 (m, 1H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give the crude product
  3. washwas eluted with CH2Cl2/MeOH

Sources & evidence

ORD record
ord-729829b23dc446a5a6cc382a8677e78c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…