Trifluoroacetic acid → HCID 71280381, compound

HRID 246478Notes

Reaction equation

HRID 246478 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]3[C:25]4[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=4)[CH:19]=[N:18]3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]3[C:25]4[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=4)[CH:19]=[N:18]3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71280533HCID 71280533, compound

Product 1

HCID 71280381HCID 71280381, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-tert-butyl-2-(5-fluoro-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (120 mg, 249 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1 mL). After 15 h, the mixture was concentrated in vacuo then 25 mL Jan. 10, 1960 of a solution of ammonium hydroxide/methanol/dichloromethane was added. After 1 h the mixture was concentrated in vacuo then purified by chromatography (silica, 24 g Analogix column, 0-5% methanol containing 10% ammonium hydroxide in dichloromethane) to give 2-(5-fluoro-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (24.4 mg, 28%). MS: (M+H)+=353; 1H NMR (DMSO-d6) δ: 9.02 (s, 1H), 8.56-8.61 (m, 2H), 8.53 (d, J=0.8 Hz, 2H), 8.42 (d, J=3.0 Hz, 1H), 7.78 (dd, J=8.8, 2.3 Hz, 1H), 7.62 (s, 1H), 7.49 (d, J=2.5 Hz, 1H), 1.50 (s, 9H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. addition10, 1960 of a solution of ammonium hydroxide/methanol/dichloromethane was added
  3. concentrationAfter 1 h the mixture was concentrated in vacuo
  4. customthen purified by chromatography (silica, 24 g Analogix column, 0-5% methanol containing 10% ammonium hydroxide in dichloromethane)

Sources & evidence

ORD record
ord-3da643be29dc4c0c98f2712aa6990adc
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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