Trifluoroacetic acid → (r)-6-Methyl-imidazo[2,1-b]thiazole-5-carboxylic acid piperidin-3-ylamide

HRID 1094260Notes

Reaction equation

HRID 1094260 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9]=1[C:10]([NH:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15](C(O)=O)[CH2:14]1)=[O:11])[CH:7]=[CH:6][S:5]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:15]1[CH2:16][CH2:17][CH2:18][C@@H:13]([NH:12][C:10]([C:9]2[N:8]3[C:4]([S:5][CH:6]=[CH:7]3)=[N:3][C:2]=2[CH3:1])=[O:11])[CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 131729496(R)-3-[(6-methyl-imidazo[2,1-b]thiazole-5-carbonyl)-amino]-piperidine-1-carboxylic acid

Product 1

HCID 66639497(r)-6-Methyl-imidazo[2,1-b]thiazole-5-carboxylic acid piperidin-3-ylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (˜0° C.) solution of (R)-3-[(6-methyl-imidazo[2,1-b]thiazole-5-carbonyl)-amino]-piperidine-1-carboxylic acid tent-butyl ester (1.47 g) in dry DCM (30 mL) was added slowly TFA (4.63 mL). The reaction mixture was stirred at RT for 20 h, 5 eq more of TFA (4.63 mL) was added and the stirring was continued for 2 h. The reaction was concentrated in vacuo to yield the title compound as a bis-trifluoroacetate salt which was used for the next step without further purification.

Workup

  1. waitthe stirring was continued for 2 h
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-0e9e656e20804b2883c67485b4c3ef7c
Source dataset
uspto-grants-2012_03
Patent number
US08133901B2

Reaction notes

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