Hydrazine hydrate (1:1) → HCID 46214650, compound

HRID 2367187Notes

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][CH2:20][CH2:19][CH2:18]2)[N:3]=1.O.[NH2:24][NH2:25]>CCO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:11]([C:12]([NH2:13])=[N:24][NH:25]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

In a 25 mL sealable tube under argon were combined 4-[2-amino-6-(1-piperidinyl)-4-pyrimidinyl]-2-fluorobenzonitrile (0.106 g, 0.258 mmol), hydrazine monohydrate (0.51 mL, 10.3 mmol) and EtOH (5 mL). The vial was sealed and the reaction mixture was stirred overnight at 95° C. The reaction was cooled to room temperature and concentrated. The resulting solid was sonicated on a mixture of EtOH (1 mL) and water (9 mL). The mixture was filtered and the solid was washed with water and dried under vacuum at 40° C. to afford the title compound (66 mg, 80%) as a white solid. LC-MS (ES) m/z=310 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.53 (m, 4H), 1.64 (m, 2H), 3.47-3.79 (m, 4H), 5.37 (s, 2H), 6.03 (s, 2H), 6.58 (s, 1H), 7.57 (dd, J=8.3, 1.3 Hz, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.94 (s, 1H), 11.49 (s, 1H).

Workup

customIn a 25 mL sealable tube under argon were combined
customThe vial was sealed
temperatureThe reaction was cooled to room temperature
concentrationconcentrated
customThe resulting solid was sonicated on a mixture of EtOH (1 mL) and water (9 mL)
filtrationThe mixture was filtered
washthe solid was washed with water
customdried under vacuum at 40° C.

Sources & evidence

ORD record: ord-ecb6ec2998234a52a991428c029ee328
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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