Trifluoroacetic acid → HCID 67327163, compound

HRID 1500748Notes

Reaction equation

HRID 1500748 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[N:24]=[C:23]([NH:25][C@@H:26]4[CH2:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]4)[CH:22]=[CH:21][N:20]=3)=[C:12]2[CH:11]=1)#[N:9].C(=O)([O-])O.[Na+]>ClCCl>[NH:28]1[CH2:29][CH2:30][CH2:31][C@@H:26]([NH:25][C:23]2[CH:22]=[CH:21][N:20]=[C:19]([C:18]3[CH:17]=[N:16][N:13]4[CH:14]=[CH:15][C:10]([C:8]#[N:9])=[CH:11][C:12]=34)[N:24]=2)[CH2:27]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2×HCID 67326745HCID 67326745, compound

Product 1

HCID 67327163HCID 67327163, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.61 mL, 7.97 mmol) was added to a stirred solution of (R)-tert-butyl 3-(2-(5-cyanopyrazolo[1,5-a]pyridin-3-yl)pyrimidin-4-ylamino)piperidine-1-carboxylate (Preparation 7a, 0.12 g, 0.27 mmol) in dichloromethane (4 mL) and the mixture was stirred at room temperature for 4 hours. 4% Aqueous sodium hydrogencarbonate solution and solid sodium hydrogencarbonate were then added until the pH was basic and the mixture was further extracted with more dichloromethane. The organic layer was separated, dried (MgSO4) and evaporated to give the title compound (0.06 g, 62%) as a pale yellow solid which was used in the next synthetic step without further purification.

Workup

  1. extractionthe mixture was further extracted with more dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-9923845c0e06429989cdb4c4cfc45bed
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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