Cyclopropylamine → (R)-N-cyclopropyl-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 1631360Notes

Reaction equation

HRID 1631360 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](O)=[O:25])=[C:17]3[N:16]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH:27]1([NH2:30])[CH2:29][CH2:28]1>>[CH:27]1([NH:30][C:24]([C:23]2[CH:22]=[N:21][N:18]3[CH:19]=[CH:20][C:15]([N:11]4[CH2:12][CH2:13][CH2:14][C@@H:10]4[C:4]4[C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=4)=[N:16][C:17]=23)=[O:25])[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 66847769HCID 66847769, compound

Product 1

HCID 66851769(R)-N-cyclopropyl-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideYield 57%

Procedure

Prepared by the method described in Example 1 using (R)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation K) and cyclopropanamine. The combined organic extracts were concentrated and the residue was purified by reverse phase HPLC (0-70% acetonitrile/water) to provide the title compound (19 mg, 57% yield). MS (apci) m/z=397.0 (M+H).

Workup

  1. customPrepared by the method
  2. concentrationThe combined organic extracts were concentrated
  3. customthe residue was purified by reverse phase HPLC (0-70% acetonitrile/water)

Sources & evidence

ORD record
ord-4b2ff46a8d014dc58aaad698f8ef2939
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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