Trifluoroacetic acid → 5-amino-2-(2,6-difluorophenyl)-N-(5-(piperidin-4-yloxy)isothiazol-4-yl)thiazole-4-carboxamide

HRID 871039Notes

Reaction equation

HRID 871039 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=2[F:14])=[N:4][C:3]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][S:21][C:22]=1[O:23][CH:24]1[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]1)=[O:16].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]1[S:6][C:5]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=2[F:14])=[N:4][C:3]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][S:21][C:22]=1[O:23][CH:24]1[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86720858Tert-butyl 4-(4-(5-amino-2-(2,6-difluorophenyl)thiazole-4-carboxamido)isothiazol-5-yloxy)piperidine-1-carboxylate

Product 1

HCID 712619085-amino-2-(2,6-difluorophenyl)-N-(5-(piperidin-4-yloxy)isothiazol-4-yl)thiazole-4-carboxamideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(5-amino-2-(2,6-difluorophenyl)thiazole-4-carboxamido)isothiazol-5-yloxy)piperidine-1-carboxylate (1A) (10 mg, 0.02 mmol) in CH2Cl2 (1 mL) at room temperature (25° C.) was added TFA (trifluoroacetic acid) (0.5 mL), stirred for 10 min and then concentrated in vacuo at room temperature (25° C.) to afford the product 5-amino-2-(2,6-difluorophenyl)-N-(5-(piperidin-4-yloxy)isothiazol-4-yl)thiazole-4-carboxamide (1) (5 mg, 0.011 mmol)

Workup

  1. concentrationconcentrated in vacuo at room temperature (25° C.)

Sources & evidence

ORD record
ord-844eb220df7b495989493564fed9d18a
Source dataset
uspto-grants-2015_03
Patent number
US08969584B2

Reaction notes

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