Trifluoroacetic acid → 5-{3-(cyanomethyl)-3-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide

HRID 571468Notes

Reaction equation

HRID 571468 reaction equation
[C:1]([CH2:3][C:4]1([N:22]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]4[N:33](COCC[Si](C)(C)C)[CH:34]=[CH:35][C:28]=34)[CH:24]=[N:23]2)[CH2:7][N:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][C@H:17]([CH:19]3[CH2:21][CH2:20]3)[CH3:18])=[O:15])=[N:12][CH:13]=2)[CH2:5]1)#[N:2].C(O)(C(F)(F)F)=O>>[C:1]([CH2:3][C:4]1([N:22]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]4[NH:33][CH:34]=[CH:35][C:28]=34)[CH:24]=[N:23]2)[CH2:5][N:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][C@H:17]([CH:19]3[CH2:20][CH2:21]3)[CH3:18])=[O:15])=[N:12][CH:13]=2)[CH2:7]1)#[N:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 712080055-{3-(cyanomethyl)-3-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide

Product 1

HCID 711557865-{3-(cyanomethyl)-3-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide

Procedure

5-{3-(Cyanomethyl)-3-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-[(1S)-1-cyclopropylethyl]pyridine-2-carboxamide (0.350 g, 0.75 mmol) was dissolved in dichloromethylene (3 mL). To the solution was added TFA (1.5 mL). The mixture was stirred at room temperature for 2 hours. The volatiles were evaporated under reduced pressure. The residue was dissolved in methanol (5 mL), and ethylenediamine (1.0 mL) was added. The mixture was stirred at room temperature overnight, and was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=467.3.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (5 mL)
  3. additionethylenediamine (1.0 mL) was added
  4. stirringThe mixture was stirred at room temperature overnight
  5. customwas purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-04a6961d03574a72b162776188469b57
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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