Hydrazine → HCID 178488778, compound

HRID 2367370Notes

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][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[N:27]=3)[CH2:18]2)[N:3]=1.[NH2:36][NH2:37]>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:36][NH:37]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][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[N:27]=3)[CH2:18]2)[N:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 4-[2-amino-6-(2-{4-[4-(methyloxy)phenyl]-1H-imidazol-2-yl}-4-morpholinyl)-4-pyrimidinyl]-2-fluorobenzonitrile (350 mg, 0.742 mmol) and hydrazine (1.18 mL, 37.1 mmol) in ethanol (4 mL) was heated under microwave conditions with stirring for 1 hour. The mixture was concentrated. Ethanol (15 mL) was added to the resulting residue, and the resulting mixture was heated to 85° C. for 20 minutes, and then filtered while hot and dried in vacuo to afford the title compound (115 mg) as a pale yellow solid. LC-MS (ES) m/z=484 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.09-3.15 (m, 1H), 3.19-3.25 (m, 1H), 3.69-3.77 (m, 4H), 4.02-4.05 (m, 1H), 4.29-4.36 (m, 1H), 4.56-4.62 (m, 1H), 4.72 (s, 1H), 5.39 (s, 2H), 6.21 (s, 2H), 6.71 (s, 1H), 6.89-6.98 (m, 2H), 7.21-7.68 (m, 1H), 7.60-7.65 (m, 1H), 7.68-7.72 (m, 3H), 7.99 (s, 1H), 11.52 (s, 1H), 12.22-12.48 (m, 1H).

Workup

temperaturewas heated under microwave conditions
concentrationThe mixture was concentrated
additionEthanol (15 mL) was added to the resulting residue
filtrationfiltered while hot and
customdried in vacuo

Sources & evidence

ORD record: ord-1173c0a90e314c759a0b22dfc250ffe2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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