Trifluoroacetic acid → HCID 178510351, compound

HRID 40671Notes

Reaction equation

HRID 40671 reaction equation
COC1C=CC(C[N:8]2[C:16]3[CH:15]=[C:14]([NH:17][C:18]4[N:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=4)[N:13]=[CH:12][C:11]=3[N:10]=[CH:9]2)=CC=1.C(O)(C(F)(F)F)=O>>[NH:8]1[C:16]2[CH:15]=[C:14]([NH:17][C:18]3[N:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=3)[N:13]=[CH:12][C:11]=2[N:10]=[CH:9]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 442043575-(1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-ylamino)pyrazine-2-carbonitrile

Product 1

HCID 178510351HCID 178510351, compoundYield 100%

Procedure

5-(1-(4-Methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-ylamino)pyrazine-2-carbonitrile (10.6 mg, 30 μmol) was treated with TFA at 80° C. over 30 minutes. Isolation by SPE on a MP-TsOH cartridge, eluting with 2N ammonia in methanol, followed by concentration, gave the title compound as a white solid (7.02 mg, 100%). 1H NMR (d6-DMSO, 400 MHz) δ 12.79 (br s, 1H), 10.85 (br s, 1H), 8.76 (s, 2H), 8.75 (s, 1H), 8.35 (s, 1H), 8.26 (s, 1H). LCMS (2) Rt=1.36 min; m/z (ESI+) 238 (MH+), (ESI−) 236 (M−H).

Workup

  1. washIsolation by SPE on a MP-TsOH cartridge, eluting with 2N ammonia in methanol
  2. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-3a9d7cffadef40bfa1ba3e23272ac17b
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Reaction notes

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