Trifluoroacetic acid → 8-(2-Amino-6-methylbenzylamino)-3-formyl-2-methylimidazo[1,2-a]pyridine

HRID 1955011Notes

Reaction equation

HRID 1955011 reaction equation
C(OC([NH:8][C:9]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[N:15]([C:19]([CH:23]=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[NH2:8][C:9]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[N:15]([C:19]([CH:23]=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 23294184HCID 23294184, compound

Product 1

HCID 232941708-(2-Amino-6-methylbenzylamino)-3-formyl-2-methylimidazo[1,2-a]pyridine

Procedure

Starting from 8-(2-tert-butoxycarbonylamino-6-methylbenzylamino)-3-formyl-2-methylimidazo[1,2-a]pyridine (3.6 g), trifluoroacetic acid (15 ml) and anisole (5 ml) according to the procedure described for Example C1 (Method B) gives, after chromatography on silica gel (eluent: toluene/dioxane=9:1) and crystallization from ethyl acetate/cyclohexane, 2.3 g (76%) of the title compound of m.p. 230-234° C.

Workup

  1. customgives
  2. customafter chromatography on silica gel (eluent: toluene/dioxane=9:1) and crystallization from ethyl acetate/cyclohexane, 2.3 g (76%) of the title compound of m.p. 230-234° C.

Sources & evidence

ORD record
ord-b97258a394b64b42aebf9d912b7219a4
Source dataset
uspto-grants-2000_09
Patent number
US06124313

Reaction notes

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