Trifluoroacetic acid → (R)-N-(4-(4-(pyrrolidin-3-yloxy)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

HRID 873338Notes

Reaction equation

HRID 873338 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:34]=[C:10]3[C:11]([C:15]4[CH:33]=[CH:32][C:18]([O:19][C@@H:20]5[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]5)=[CH:17][CH:16]=4)=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:22]1[CH2:23][CH2:24][C@@H:20]([O:19][C:18]2[CH:17]=[CH:16][C:15]([C:11]3[C:10]4[N:9]([N:8]=[C:7]([NH:6][C:4]([CH:1]5[CH2:2][CH2:3]5)=[O:5])[CH:34]=4)[CH:14]=[CH:13][CH:12]=3)=[CH:33][CH:32]=2)[CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86710536(R)-tert-Butyl 3-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)phenoxy)pyrrolidine-1-carboxylate

Product 1

HCID 70979103(R)-N-(4-(4-(pyrrolidin-3-yloxy)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 3-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)phenoxy)pyrrolidine-1-carboxylate (0.44 g, 0.95 mmol) was stirred in DCM (10 mL) and TFA (1 mL) at room temperature for 3 h. The reaction mixture was concentrated in vacuo and loaded onto an SCX column in DCM. MeOH (100 mL) was passed through the column and the compound was eluted with (7 N NH3 in MeOH in MeOH) (1:5) (200 mL). The filtrate was concentrated in vacuo to give (R)—N-(4-(4-(pyrrolidin-3-yloxy)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washthe compound was eluted with (7 N NH3 in MeOH in MeOH) (1:5) (200 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5d2bfaf47b25468a89bd6f321f1d1c3f
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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