Hydrochloric Acid → HCID 178522413, compound

HRID 529740Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH:34]([F:36])[F:35])=[C:6]([C:8]2[N:12](COCC[Si](C)(C)C)[N:11]=[CH:10][C:9]=2[NH:21][C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[N:29][C:28]=23)=[O:23])[CH:7]=1.Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH:34]([F:36])[F:35])=[C:6]([C:8]2[C:9]([NH:21][C:22]([C:24]3[CH:25]=[N:26][N:27]4[CH:32]=[CH:31][CH:30]=[N:29][C:28]=34)=[O:23])=[CH:10][NH:11][N:12]=2)[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-(5-chloro-2-difluoromethoxyphenyl)-1-(2-trimethylsilanylethoxymethyl)-1H-pyrazol-4-yl]amide (59.0 g, 110 mmol) in methanol (420 mL) was treated with 6N HCl (80 mL) and the mixture heated at 60° C. for 4 hours. The solvent was evaporated and the residue triturated with water. The solid was collected by filtration, washed with water and left to air dry. The solid was triturated with a minimum volume of acetonitrile, collected by filtration, washed with diethyl ether and dried at 60° C. under high vacuum to afford the title compound as a yellow solid (42.9 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 9.71 (s, 1H), 9.34 (dd, 1H), 8.68-8.69 (m, 1H), 8.66 (s, 1H), 8.25 (s, 1H), 7.62 (dd, 2H), 7.43-7.46 (m, 1H), 7.29 (dd, 1H), 7.23 (d, 1H).

Workup

customThe solvent was evaporated
customthe residue triturated with water
filtrationThe solid was collected by filtration
washwashed with water
waitleft to air
customdry
customThe solid was triturated with a minimum volume of acetonitrile
filtrationcollected by filtration
washwashed with diethyl ether
customdried at 60° C. under high vacuum

Sources & evidence

ORD record: ord-8bfd11f024e34e59bf34321fac942dd0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346815B2

Reaction notes

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