Tert-butyl 4-(5-(2-phenyl-5-(trifluoromethyl)oxazole-4-carboxamido)pyridin-2-yl)piperazine-1-carboxylate → (S)-3-(5-{[2-(2-trifluoromethoxy-phenyl)-5-trifluoromethyl-oxazole-4-carbonyl]-amino}-pyrimidin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl ester

HRID 557754Notes

Reaction equation

HRID 557754 reaction equation
C(OC(N1CCN(C2C=CC(NC(C3N=C(C4C=CC=CC=4)OC=3C(F)(F)F)=O)=CN=2)CC1)=O)(C)(C)C.[C:38]([O:42][C:43]([N:45]1[CH2:49][CH2:48][C@H:47]([NH:50][C:51]2[N:56]=[CH:55][C:54]([NH:57][C:58]([C:60]3[N:61]=[C:62]([C:69]4[CH:74]=[CH:73][CH:72]=[CH:71][C:70]=4[O:75][C:76]([F:79])([F:78])[F:77])[O:63][C:64]=3[C:65]([F:68])([F:67])[F:66])=[O:59])=[CH:53][N:52]=2)[CH2:46]1)=[O:44])(C)(C)[CH3:39].FC(F)(F)OC1C=CC=CC=1C1OC(C(F)(F)F)=C(C(O)=O)N=1.C(OC(N1CC[C@H](NC2N=CC(N)=CN=2)C1)=O)C>>[CH2:38]([O:42][C:43]([N:45]1[CH2:49][CH2:48][C@H:47]([NH:50][C:51]2[N:52]=[CH:53][C:54]([NH:57][C:58]([C:60]3[N:61]=[C:62]([C:69]4[CH:74]=[CH:73][CH:72]=[CH:71][C:70]=4[O:75][C:76]([F:79])([F:78])[F:77])[O:63][C:64]=3[C:65]([F:66])([F:67])[F:68])=[O:59])=[CH:55][N:56]=2)[CH2:46]1)=[O:44])[CH3:39]

Participants

5

Reactant 4

HCID 52937267Tert-butyl 4-(5-(2-phenyl-5-(trifluoromethyl)oxazole-4-carboxamido)pyridin-2-yl)piperazine-1-carboxylateHCID 593013162-(2-Trifluoromethoxy-phenyl)-5-trifluoromethyl-oxazole-4-carboxylic acidHCID 66738673(S)-3-(5-amino-pyrimidin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl esterHCID 86629270(S)-3-(5-{[2-(2-trifluoromethoxy-phenyl)-5-trifluoromethyl-oxazole-4-carbonyl]-amino}-pyrimidin-2-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 25118301(S)-3-(5-{[2-(2-trifluoromethoxy-phenyl)-5-trifluoromethyl-oxazole-4-carbonyl]-amino}-pyrimidin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl ester

Procedure

With a method similar to that used for the preparation of 4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester above, (S)-3-(5-{[2-(2-trifluoromethoxy-phenyl)-5-trifluoromethyl-oxazole-4-carbonyl]-amino}-pyrimidin-2-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester was prepared from 2-(2-trifluoromethoxy-phenyl)-5-trifluoromethyl-oxazole-4-carboxylic acid and (S)-3-(5-amino-pyrimidin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl ester. LCMS calcd for C23H20F6N6O5 (m/e) 574.4, obsd 575.2 (M+H).

Sources & evidence

ORD record
ord-1089c91339b84c19845b5fa01db04e66
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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