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

HRID 873332Notes

Reaction equation

HRID 873332 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:36]=[C:10]3[C:11]([C:15]4[CH:35]=[CH:34][C:18]([CH2:19][N:20]5[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][C@H:21]5[CH3:33])=[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>[CH3:33][C@@H:21]1[CH2:22][NH:23][CH2:24][CH2:25][N:20]1[CH2:19][C:18]1[CH:17]=[CH:16][C:15]([C:11]2[C:10]3[N:9]([N:8]=[C:7]([NH:6][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])[CH:36]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86710533(R)-tert-butyl 4-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)benzyl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 70979626(R)-N-(4-(4-((2-methylpiperazin-1-yl)methyl)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 4-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)benzyl)-3-methylpiperazine-1-carboxylate (162 mg, 0.33 mmol) was stirred in DCM (2 mL) and TFA (0.3 mL) at room temperature for 2 h. The reaction mixture was concentrated in vacuo and loaded onto an SCX column in DCM. MeOH (20 mL) was passed through the column and the compound was eluted with (7 N NH3 in MeOH in MeOH) (1:5) (50 mL). The filtrate was concentrated in vacuo to give (R)—N-(4-(4-((2-methylpiperazin-1-yl)methyl)phenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washthe compound was eluted with (7 N NH3 in MeOH in MeOH) (1:5) (50 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-939b1ac7c44e42c781af350921c3d531
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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