Hydrochloric Acid → HCID 72703417, compound

HRID 2207382Notes

Reaction equation

[O-:1][C:2]#[N:3].[K+].Cl.[CH3:6][C:7]1[CH:8]=[C:9]([C:24]2[CH:25]=[C:26]([C:30]3([OH:36])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH:27]=[N:28][CH:29]=2)[CH:10]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=2)[CH:12]=1.[NH4+].[OH-]>C1COCC1.O>[OH:36][C:30]1([C:26]2[CH:27]=[N:28][CH:29]=[C:24]([C:9]3[CH:10]=[C:11]([NH:13][C:14]4[N:19]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:17]=[CH:16][N:15]=4)[CH:12]=[C:7]([CH3:6])[CH:8]=3)[CH:25]=2)[CH2:31][CH2:32][N:33]([C:2]([NH2:3])=[O:1])[CH2:34][CH2:35]1

Participants

Conditions

Temperature: 50 °C

Procedure

Potassium cyanate (11.9 mg, 0.147 mmol) and HCl (138 μL, 0.138 mmol) was added to the 4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]piperidin-4-ol (50.0 mg, 0.092 mmol) in THF (383 μL) and water (1.15 mL) and heated to 50° C. for 4 hours. The reaction mixture was cooled to room temperature and neutralize with aqueous 10% NH4OH. The resulting precipitate was collected by filtration to yield 4-hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]piperidine-1-carboxamide. MS APCI calc'd for C23H24F3N6O2 [M+H]+ 473. found 473. 1H NMR (500 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.82 (d, J=5.2 Hz, 1H), 8.68 (dd, J=2.4 Hz, 6.3 Hz, 2H), 8.02 (s, 1H), 7.97 (s, 1H), 7.56 (s, 1H), 7.25 (d, J=10.2 Hz, 1H), 7.22 (s, 1H), 5.92 (s, 2H), 3.85 (d, J=16.4 Hz, 2H), 3.09 (t, J=14.5 Hz, 2H), 2.36 (s, 3H), 1.88 (t, J=15.9 Hz, 2H), 1.63 (d, J=14.3 Hz, 2H).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-079637d42aa144ffad1c986e7c79aa95
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376418B2

Reaction notes

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