Trifluoroacetic acid → 2-imidazo[1,2-a]pyridin-3-yl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide

HRID 246240Notes

Reaction equation

[C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:39])[C@H:8]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[N:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]5=[N:24][CH:23]=4)[N:20]=3)[N:15](COCC[Si](C)(C)C)[CH:14]=2)=[O:12])[CH3:9])[CH2:4]1)#[N:2].C(O)(C(F)(F)F)=O>>[C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:39])[C@H:8]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[N:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]5=[N:24][CH:23]=4)[N:20]=3)[NH:15][CH:14]=2)=[O:12])[CH3:9])[CH2:4]1)#[N:2]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 712857092-Imidazo[1,2-a]pyridin-3-yl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide

Product 1

HCID 712887342-imidazo[1,2-a]pyridin-3-yl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide

Procedure

2-Imidazo[1,2-a]pyridin-3-yl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide was deprotected using the described two step procedure (TFA followed by aqueous base) followed by chromatography to give 2-imidazo[1,2-a]pyridin-3-yl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide. (ES+): 414. 1H NMR (300 MHz, DMSO-d6) δ: 12.9 (m, 1H, 9.86 (m, 1H) 9.11 (s, 1H) 8.57 (s, 1H) 8.42 (d, 1H) 8.34 (d, 1H) 7.78 (d, 1H) 7.47 (t, 1H) 7.19 (m, 1H) 4.65 (m, 1H) 4.13 (m, 2H) 3.89 (m, 2H) 3.78 (m, 1H) 1.39 (d, 3H)

Sources & evidence

ORD record: ord-d4099bea6688422a9c8c2e4fb65afad4
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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