Hydrazine → 6-{2-Amino-6-[2-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-4-morpholinyl]-4-pyrimidinyl}-1H-indazol-3-amine

HRID 2367347Notes

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:27][C:26]4[CH2:28][CH2:29][CH2:30][CH2:31][C:25]=4[N:24]=3)[CH2:18]2)[N:3]=1.[NH2:32][NH2:33]>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:32][NH:33]3)=[CH:10][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]4[CH2:31][CH2:30][CH2:29][CH2:28][C:26]=4[N:27]=3)[CH2:18]2)[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-{2-amino-6-[2-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (150 mg, 0.358 mmol) and hydrazine (1.13 mL, 35.8 mmol) in ethanol (4 mL) was heated at 120° C. under microwave conditions with stirring for 1 hour. The solvent was evaporated to get 200 mg of residue, which was purified by preparative HPLC to afford the title compound (42 mg) as a yellow powder. LC-MS (ES) m/z=432 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.71 (s, 4H), 2.42 (s, 2H), 3.12-2.99 (m, 2H), 3.66 (dt, J=11.6 Hz, 2.4 Hz, 1H), 4.00 (dd, J=11.6 Hz, 2.0 Hz, 1H), 4.33-4.30 (m, 1H), 4.44 (dd, J=10.8 Hz, 2.4 Hz, 1H), 4.62 (bs, 1H), 5.28 (s, 2H), 6.18 (s, 2H), 6.66 (s, 1H), 7.61 (dd, J=8.4 Hz, 0.8 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.97 (s, 1H), 11.51 (s, 1H), 11.68 (s, 1H).

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-15bfefe964294a1fb534b3419c7c0601
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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