Hydrazine hydrate (1:1) → HCID 58504537, compound

HRID 2367619Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([NH:15][CH3:16])[N:12]=[C:11]([N:17]3[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:18]3)[CH:10]=2)=[CH:5][C:4]=1F)#[N:2].O.[NH2:34][NH2:35]>C(O)C>[NH2:2][C:1]1[C:3]2[C:4](=[CH:5][C:6]([C:9]3[N:14]=[C:13]([NH:15][CH3:16])[N:12]=[C:11]([N:17]4[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23][C:24](=[O:31])[C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:18]4)[CH:10]=3)=[CH:7][CH:8]=2)[NH:35][N:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To N-{(3R)-1-[6-(4-cyano-3-fluorophenyl)-2-(methylamino)-4-pyrimidinyl]-3-piperidinyl}benzamide (83 mg, 0.19 mmol) in ethanol (2 mL) was added hydrazine monohydrate (0.5 mL, 10.2 mmol), and the reaction mixture was stirred overnight at 100° C. into a sealed tube. The solution was poured onto water (˜50 mL) and a precipitate formed. The aqueous mixture was filtered, and the solid was further washed with water. The material was dried under vacuum overnight at 45° C. to afford the title compound (52 mg) as an off-white solid. LC-MS (ES) m/z=443 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.43-1.60 (m, 1H), 1.61-1.75 (m, 1H), 1.76-1.89 (m, 1H), 1.92-2.05 (m, 1H), 2.83 (d, J=4.0 Hz, 3H), 2.91-3.10 (m, 2H), 3.83-3.98 (m, 1H), 4.24-4.57 (m, 2H), 5.38 (s, 2H), 6.45-6.58 (m, 1H), 6.64 (s, 1H), 7.41-7.49 (m, 2H), 7.50-7.56 (m, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.71 (d, J=8.34 Hz, 1H), 7.82-7.90 (m, 2H), 7.98 (bs, 1H), 8.37 (d, J=7.6 Hz, 1H), 11.50 (s, 1H).

Workup

additionThe solution was poured onto water (˜50 mL)
customa precipitate formed
filtrationThe aqueous mixture was filtered
washthe solid was further washed with water
customThe material was dried under vacuum overnight at 45° C.

Sources & evidence

ORD record: ord-810e4f613b4e4ec88cc6bd488aa5ebda
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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