Hydrochloric Acid → 7-Amino-5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 2047161Notes

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][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:9]=1[C:33]#[N:34].Cl>CCO>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:9]=1[C:33]#[N:34]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile (5 mg), EtOH (1 mL) and 3N HCl (1 mL) was heated at 60° C. until LCMS indicated the completed reaction. The mixture was cooled to room temperature and the solvent was evaporated in vacuo. Purification by prep-LC afforded the desired compound. LCMS tR=3.12 Min (UV254nm). Mass calculated for, M+ 371.1, observed LC/MS m/z 372.2 (M+H).

Workup

customthe completed reaction
temperatureThe mixture was cooled to room temperature
customthe solvent was evaporated in vacuo
customPurification

Sources & evidence

ORD record: ord-a1250c9cfa9a49328077e774ded415a1
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

Loading…