Trifluoroacetic acid → Methyl 2-(2-(2-(2-((2-fluoro-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate

HRID 705781Notes

Reaction equation

C(O[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[CH:11][C:10]=1[F:28])=O)(C)(C)C.CS(C1[N:38]=[C:37]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[CH2:47][C:48]([O:50][CH3:51])=[O:49])[C:36]([C:52]([F:55])([F:54])[F:53])=[CH:35][N:34]=1)(=O)=O.C(O)(C(F)(F)F)=O>FC(F)(F)CO>[F:28][C:10]1[CH:11]=[C:12]([CH:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)[CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[N:38]=[C:37]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[CH2:47][C:48]([O:50][CH3:51])=[O:49])[C:36]([C:52]([F:53])([F:54])[F:55])=[CH:35][N:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of tert-butyl 4-(4-((tert-butoxycarbonyl)amino)-3-fluorophenyl)piperidine-1-carboxylate (I57) (0.376 g, 0.954 mmol) and methyl 2-(2-(2-(2-(methylsulfonyl)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate (I15) (0.268 g, 0.667 mmol) in 2,2,2-trifluoroethanol (15 mL) was added TFA (0.8 mL). The resulting mixture was heated under microwave irradiation at 100° C. for 20 minutes then 15 minutes then concentrated under reduced pressure to give a crude sample of the title compound (I58) (0.344 g) which was used without purification.

Workup

concentration15 minutes then concentrated under reduced pressure

Sources & evidence

ORD record: ord-96ec1f23497f4089a53f845bfa7efe06
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174946B2

Reaction notes

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