Hydrochloric Acid → HCID 56646547, compound

HRID 1773611Notes

Reaction equation

HRID 1773611 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C@H:22]2[CH2:26][O:25]C(C)(C)[O:23]2)=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=23)=[O:10])[CH:7]=1.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C@H:22]([OH:23])[CH2:26][OH:25])=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=23)=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66664792HCID 66664792, compound

Product 1

HCID 56646547HCID 56646547, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-chloro-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-amide (40 mg) and an aqueous solution of hydrochloric acid (2 M, 5 mL) in tetrahydrofuran (5 mL) was heated at 70° C. for 15 minutes. The resulting mixture was cooled and the solid formed was collected by filtration, washed with a diluted aqueous solution of sodium hydroxide and with water, dried in a vacuum oven to give 30 mg of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-chloro-2-((R)-2,3-dihydroxy-propoxy)-phenyl]-amide as a white solid. MS=362 [M]+.

Workup

  1. temperatureThe resulting mixture was cooled
  2. customthe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with a diluted aqueous solution of sodium hydroxide and with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-c04ebc6cbdc34f4aaa257d2ccc54f315
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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