Trifluoroacetic acid → 3-[5-(3-Methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]azepan-2-one

HRID 1040182Notes

Reaction equation

HRID 1040182 reaction equation
COC1C=CC(C[N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:15]3[S:16][C:17]([C:20]4[CH:25]=[C:24]([NH:26][C:27]5[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=5)[CH:23]=[C:22]([CH3:37])[CH:21]=4)=[CH:18][N:19]=3)[C:9]2=[O:38])=CC=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>ClCCl>[CH3:37][C:22]1[CH:21]=[C:20]([C:17]2[S:16][C:15]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][NH:8][C:9]3=[O:38])=[N:19][CH:18]=2)[CH:25]=[C:24]([NH:26][C:27]2[N:32]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:30]=[CH:29][N:28]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 67432380HCID 67432380, compound

Product 1

HCID 584562383-[5-(3-Methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]azepan-2-oneYield 27.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a microwave vial, were added the product of Step 2 (44.4 mg, 0.078 mmol), trifluoroacetic acid (0.3 ml, 3.89 mmol), trifluoromethanesulfonic acid (10 μl, 0.078 mmol) and dichloromethane (1 ml). The mixture was irradiated at 110° C. in the microwave for 40 min. The mixture was then purified by reverse phase HPLC to afford the title compound (12 mg, 0.021 mmol, 27.3% yield).

Workup

  1. customThe mixture was irradiated at 110° C. in the microwave for 40 min
  2. customThe mixture was then purified by reverse phase HPLC

Sources & evidence

ORD record
ord-1ef15baab10f44a8b5b0b3c6331478ac
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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