Trifluoroacetic acid → Trifluoroacetic acid

HRID 570314Notes

Reaction equation

HRID 570314 reaction equation
[N:1]1[CH:2]=[C:3]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:20]3[N:24]=[C:23]([C:25]4([NH:29]C(=O)OC(C)(C)C)[CH2:28][O:27][CH2:26]4)[O:22][N:21]=3)[CH:16]=[CH:17][C:18]=2[CH3:19])=[O:11])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>>[NH2:29][C:25]1([C:23]2[O:22][N:21]=[C:20]([C:15]3[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([NH:12][C:10]([C:3]4[N:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]5=[N:1][CH:2]=4)=[O:11])[CH:14]=3)[N:24]=2)[CH2:26][O:27][CH2:28]1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71281075Tert-butyl (3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)oxetan-3-yl)carbamate

Product 2

HCID 6422Trifluoroacetic acidHCID 71281406N-(5-(5-(3-aminooxetan-3-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

Procedure

(3-(3-(3-(Imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)oxetan-3-yl)carbamate (46) (29.5 mg, 0.06 mmol) was dissolved in TFA (0.5 mL) and stirred at room temperature for 10 minutes. Then TFA was removed under vacuum to yield crude N-(5-(5-(3-aminooxetan-3-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (47) as a TFA salt which was used without further purification. MS m/z 391.1 (M+1)+.

Workup

  1. customThen TFA was removed under vacuum

Sources & evidence

ORD record
ord-6c9113292926454a9b1561e9f7255362
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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