3,3,3-Trifluoropropionyl chloride → N-(3-(benzo[d]thiazol-2-yl)-6-fluoroimidazo[1,2-a]pyridin-2-yl)-3,3,3-trifluoropropanamide

HRID 556320Notes

Reaction equation

HRID 556320 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[NH2:20].[F:21][C:22]([F:28])([F:27])[CH2:23][C:24](Cl)=[O:25]>N1C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[NH:20][C:24](=[O:25])[CH2:23][C:22]([F:28])([F:27])[F:21]

Participants

4

Reactant 2

HCID 27833433,3,3-Trifluoropropionyl chlorideHCID 576074763-(Benzo[d]thiazol-2-yl)-6-fluoroimidazo[1,2-a]pyridin-2-amine2×

Product 1

HCID 57607471N-(3-(benzo[d]thiazol-2-yl)-6-fluoroimidazo[1,2-a]pyridin-2-yl)-3,3,3-trifluoropropanamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(benzo[d]thiazol-2-yl)-6-fluoroimidazo[1,2-a]pyridin-2-amine (compound m, 250 mg, 0.0009 mol) in pyridine (0.2 mL) was treated with 3,3,3-trifluoropropionyl chloride (0.134 mL, 0.0011 mol) and shaken at room temperature for about 45 min. The solvent was removed and the crude product was purified by column chromatography (50% ethyl acetate/hexane) to give N-(3-(benzo[d]thiazol-2-yl)-6-fluoroimidazo[1,2-a]pyridin-2-yl)-3,3,3-trifluoropropanamide as a white solid. Rf 0.32, 70% ethyl acetate/hexanes; MS m/z 395 (M+H). SH-SY5Y_EC50 (μM): 2.1258.

Workup

  1. customThe solvent was removed
  2. customthe crude product was purified by column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d591561aa1854cb4ac513b3a209cda97
Source dataset
uspto-grants-2011_11
Patent number
US08058274B2

Reaction notes

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