Hydrochloric Acid → HCID 56848597, compound

HRID 334375Notes

Reaction equation

C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][N:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:21]=3)=[C:12]2[N:11]=[C:10]([CH:28]2[CH2:33][CH2:32][C:31]([CH2:35][OH:36])([OH:34])[CH2:30][CH2:29]2)[C:9]=1[Br:37].Cl>O1CCOCC1>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][N:20]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:21]=3)=[C:12]2[N:11]=[C:10]([CH:28]2[CH2:33][CH2:32][C:31]([CH2:35][OH:36])([OH:34])[CH2:30][CH2:29]2)[C:9]=1[Br:37]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(1-phenyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol (542 mg, 0.729 mmol) in dioxane (4 mL) was added HCl (4 N, aq, 4 mL) at rt. The resulting mixture was stirred at 40° C. for 1 h. The reaction mixture was evaporated to dryness to afford 4-(7-amino-6-bromo-3-(1-phenyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol as a gray solid (296 mg), which was used without further purification. HPLC-MS TR=1.08 min (UV 254 nm, 3 min method); mass calculated for formula C22H23BrN6O2 482.1, observed LCMS m/z 483.1 (M+H).

Workup

customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record: ord-5061d2e28f214fd0b392950df1d49455
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883801B2

Reaction notes

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