Hydrochloric Acid → (R)-N-(3-chloropropyl)-5-(2-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)-N-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1426933Notes

Reaction equation

HRID 1426933 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:32])[C:7]([C:9]1[CH:10]=[N:11][N:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[C:23]3[C:24]([O:30]C)=[N:25][CH:26]=[C:27]([F:29])[CH:28]=3)=[N:14][C:13]=12)=[O:8]>C(#N)C>[Cl:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:32])[C:7]([C:9]1[CH:10]=[N:11][N:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[C:23]3[C:24](=[O:30])[NH:25][CH:26]=[C:27]([F:29])[CH:28]=3)=[N:14][C:13]=12)=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67470673(R)-N-(3-chloropropyl)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)-N-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 67470639(R)-N-(3-chloropropyl)-5-(2-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)pyrrolidin-1-yl)-N-methylpyrazolo[1,5-a]pyrimidine-3-carboxamideYield 150%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of HCl (4 N dioxane, 4 mL, 16.0 mmol) and (R)-N-(3-chloropropyl)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)-N-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide (100 mg, 0.224 mmol) was sealed in a pressure tube and heated at 90° C. for 90 minutes. The reaction mixture was then diluted with acetonitrile and concentrated to yield the crude product, which was carried to the next step without further purification (145 mg, 150% yield). MS (apci) m/z=433.0 (M+H).

Workup

  1. customwas sealed in a pressure tube
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-31017785c4ea47febdb8ff02f667690d
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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