Trifluoroacetic acid → Trifluoroacetate

HRID 1962684Notes

Reaction equation

HRID 1962684 reaction equation
[CH3:1][C:2]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[N:19](COCC[Si](C)(C)C)[CH:20]=[CH:21][C:14]=23)[CH:10]=[N:9]1)([CH3:7])[CH2:3][CH2:4][C:5]#[N:6].[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]>>[CH3:1][C:2]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[NH:19][CH:20]=[CH:21][C:14]=23)[CH:10]=[N:9]1)([CH3:7])[CH2:3][CH2:4][C:5]([NH2:6])=[O:31].[F:33][C:32]([F:35])([F:34])[C:30]([O-:36])=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574775834-Methyl-4-[4-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]pentanenitrile

Product 2

HCID 84468TrifluoroacetateYield 58%HCID 17754733HCID 17754733, compound

Procedure

The crude 4-methyl-4-[4-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]pentanenitrile (36 mg, 0.000088 mol, see preparation in Example 59), was stirred in TFA (2 mL) for 1 hour. The mixture was concentrated to remove excess TFA, and the resulting residue was stirred in 2 mL methanol containing 0.5 mL NH4OH for 16 hours. The product was purified by preparative-HPLC (C18 eluting with a gradient of ACN/H2O containing 0.1% TFA) to afford 4-methyl-4-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]pentanamide as the trifluoro-acetate salt (21 mg, 58%). 1H NMR (400 MHz, d6-DMSO): 12.18 (s, 1H), 8.60 (s, 1H), 8.33-8.21 (m, 2H), 7.62 (br s, 1H), 7.53 (d, 1H), 7.22 (br s, 1H), 7.04 (br s, 1H), 6.71 (br s, 1H), 2.14-2.07 (m, 2H), 1.86-1.79 (m, 2H), 1.58 (s, 6H); MS (ES): 298 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove excess TFA
  3. customThe product was purified by preparative-HPLC (
  4. washC18 eluting with a gradient of ACN/H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-b08e99ce9ce14a8b9ff46062291e7efa
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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