Hydrochloric Acid → HCID 178523335, compound

HRID 1426909Notes

Reaction equation

HRID 1426909 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([NH:26][CH2:27][CH2:28][CH2:29]O)=[O:25])=[C:17]3[N:16]=2)[C:5]([O:8]C)=[N:6][CH:7]=1.[ClH:31]>>[Cl:31][CH2:29][CH2:28][CH2:27][NH:26][C:24]([C:23]1[CH:22]=[N:21][N:18]2[CH:19]=[CH:20][C:15]([N:11]3[CH2:12][CH2:13][CH2:14][C@@H:10]3[C:4]3[C:5]([OH:8])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:16][C:17]=12)=[O:25]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67471053(R)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)-N-(3-hydroxypropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 178523335HCID 178523335, compoundYield 106%

Conditions

Temperature
85 °C

Procedure

A mixture of (R)-5-(2-(5-fluoro-2-methoxy pyridin-3-yl)pyrrolidin-1-yl)-N-(3-hydroxypropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (20 mg, 0.0483 mmol) in HCl (4 N dioxane, 1.2 mL, 4.83 mmol) was heated at 85° C. overnight. The reaction mixture was concentrated, triturated with ether, and filtered, to provide the crude product as a beige solid, which was directly used in the next step without further purification (22 mg, 106% yield). MS (apci) m/z=419.1 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-092f95841689494f89b2c851eeb931e3
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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