Trifluoroacetic acid → 2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1-cyclopropyl-ethyl)-amide

HRID 246136Notes

Reaction equation

HRID 246136 reaction equation
[CH:1]1([C@@H:4]([NH:6][C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[C:26]5[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=5)[N:20]([CH3:28])[N:19]=4)[N:16]=3)[N:11](COCC[Si](C)(C)C)[CH:10]=2)=[O:8])[CH3:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C@@H:4]([NH:6][C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[C:26]5[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=5)[N:20]([CH3:28])[N:19]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:8])[CH3:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 712883022-(6-Chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1-cyclopropyl-ethyl)-amide

Product 1

HCID 712882782-(6-Chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1-cyclopropyl-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1-cyclopropyl-ethyl)-amide (70 mg, 0.134 mmol), 2 mL of dichloromethane and 2 mL of trifluoroacetic acid was stirred 1 h, then concentrated to a yellow solid. The solid was dissolved in 2 mL of dichloromethane and 1 mL of ethylenediamine, and the yellow solution was stirred 30 min. Water (20 mL) was added. The resultant precipitate was isolated by Buchner filtration, rinsing well with water then dichloromethane, and dried by air then in vacuo to afford 33 mg (56%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3b]pyrazine-7-carboxylic acid ((S)-1-cyclopropyl-ethyl)-amide as a pale yellow solid. MS: (M+Na)+=417; 1H NMR (300 MHz, DMSO-d6) δ ppm 9.10 (s, 1 H), 8.46 (d, J=8.69 Hz, 1H), 8.42 (s, 1H), 8.14 (d, J=7.93 Hz, 1H), 8.00 (d, J=1.51 Hz, 1H), 7.27 (dd, J=8.50, 1.70 Hz, 1H), 4.17 (s, 3H), 3.55-3.70 (m, 1H), 1.34 (d, J=6.80 Hz, 3H), 1.00-1.16 (m, 1H), 0.56 (td, J=8.31, 3.40 Hz, 1H), 0.42-0.50 (m, 1H), 0.26-0.41 (m, 2H).

Workup

  1. concentrationconcentrated to a yellow solid
  2. dissolutionThe solid was dissolved in 2 mL of dichloromethane
  3. additionWater (20 mL) was added

Sources & evidence

ORD record
ord-f036a09cfe2746dbb132c509b811bb86
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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