Hydrochloric Acid → HCID 66664559, compound

HRID 1773607Notes

Reaction equation

HRID 1773607 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[NH:23][C:24]([C:26]2[CH:27]=[N:28][N:29]3[CH:34]=[CH:33][CH:32]=[N:31][C:30]=23)=[O:25])[CH2:11][CH2:10]1)=O)(C)(C)C>ClCCl>[ClH:22].[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH:12]2[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]2)=[C:17]([NH:23][C:24]([C:26]2[CH:27]=[N:28][N:29]3[CH:34]=[CH:33][CH:32]=[N:31][C:30]=23)=[O:25])[CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66664551HCID 66664551, compound

Product 1

HCID 66664559HCID 66664559, compoundYield 144.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of hydrochloric acid (1 M in E2O, 10 mL) was added, at room temperature, to a solution of 4-{4-chloro-2-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)-amino]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester (0.2 g, 0.424 mmol) in dichloromethane (5 mL) and the resulting mixture was stirred at room temperature for 60 hours. The solid formed was collected by filtration and washed once with dichloromethane, 3 times with methanol, once again with dichloromethane and once with hexane, then was dried in a vacuum oven at 60° C. to afford 125 mg (72% yield) of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-chloro-2-(piperidin-4-yloxy)-phenyl]-amide hydrochloride salt as an off-white solid. MS=372 [M+H]+.

Workup

  1. customThe solid formed
  2. filtrationwas collected by filtration
  3. washwashed once with dichloromethane, 3 times with methanol, once again with dichloromethane and once with hexane
  4. customwas dried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-d85cc372ecc14021a8a1b7fa9f526632
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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