Hydrazine hydrate (1:1) → HCID 46214649, compound

HRID 2367189Notes

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

Participants

Conditions

Temperature: 95 °C

Procedure

In a 25 mL sealable tube was dissolved 4-[2-amino-6-(cyclopentylamino)-4-pyrimidinyl]-2-fluorobenzonitrile (0.476 g, 1.16 mmol) in EtOH (10 mL). Hydrazine monohydrate (1.14 mL, 23.1 mmol) was added, the vial was sealed, and the reaction mixture was stirred for 16 hours at 95° C. The reaction was cooled to room temperature and concentrated. The resulting yellow solid was dissolved in EtOH (2 mL). Water (8 mL) was added, and the resulting mixture was sonicated for 10 minutes. The resulting white precipitate was filtered and dried to afford the title compound (177 mg, 47%) as a white solid. LC-MS (ES) m/z=310 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.38-1.61 (m, 4H), 1.61-1.78 (m, 2H), 1.92 (m, 2H), 4.22 (bs, 1H), 5.37 (s, 2H), 5.97 (bs, 2H), 6.26 (s, 1H), 6.87 (bs, 1H), 7.40 (d, J=8.6 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.82 (s, 1H), 11.51 (s, 1H).

Workup

customthe vial was sealed
temperatureThe reaction was cooled to room temperature
concentrationconcentrated
dissolutionThe resulting yellow solid was dissolved in EtOH (2 mL)
additionWater (8 mL) was added
customthe resulting mixture was sonicated for 10 minutes
filtrationThe resulting white precipitate was filtered
customdried

Sources & evidence

ORD record: ord-8ffd1e3813974e3cbe5275b7bb5dc238
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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