Acetic Acid → (R)-tert-butyl 4-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)benzyl)-3-methylpiperazine-1-carboxylate

HRID 873331Notes

Reaction equation

HRID 873331 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[CH:17]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1)=O.[CH3:24][C@H:25]1[NH:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]1.C(O)(=O)C>C(Cl)Cl>[CH:21]1([C:19]([NH:18][C:16]2[CH:17]=[C:10]3[C:9]([C:6]4[CH:5]=[CH:4][C:3]([CH2:1][N:30]5[CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:26][C@H:25]5[CH3:24])=[CH:8][CH:7]=4)=[CH:14][CH:13]=[CH:12][N:11]3[N:15]=2)=[O:20])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 86710532N-(4-(4-formylphenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-(4-Formylphenyl)pyrazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide (122 mg, 0.4 mmol), (R)-tert-butyl 3-methylpiperazine-1-carboxylate (120 mg, 0.6 mmol) and (polystyrylmethyl)trimethylammonium cyanoborohydride (loading 4 mmol/g, 0.3 g, 1.2 mmol) were shaken in DCM (15 mL) and acetic acid (1.5 mL) at room temperature for 5 d. The beads were filtered off and the filtrate concentrated in vacuo to give (R)-tert-butyl 4-(4-(2-(cyclopropanecarboxamido)pyrazolo[1,5-a]pyridin-4-yl)benzyl)-3-methylpiperazine-1-carboxylate which was used in the next step without further purification.

Workup

  1. filtrationThe beads were filtered off
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-ad1d24971f054562b824ff15c31b9faa
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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