2-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acid → 1-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyrimidin-2-yl}-piperidine-4-carboxylic acid ethyl ester

HRID 1510268Notes

Reaction equation

HRID 1510268 reaction equation
C(OC(C1CC[N:9](C2C=CC(NC(C3N=C(C4C=CC=CC=4)OC=3C(F)(F)F)=O)=CC=2)CC1)=O)C.[CH2:36]([O:38][C:39]([CH:41]1[CH2:46][CH2:45][N:44]([CH:47]2C[CH2:51][CH:50]([NH:53][C:54]([C:56]3[N:57]=[C:58]([C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)[O:59][C:60]=3[C:61]([F:64])([F:63])[F:62])=[O:55])[CH2:49][NH:48]2)[CH2:43][CH2:42]1)=[O:40])[CH3:37].C1(C2OC(C(F)(F)F)=C(C(O)=O)N=2)C=CC=CC=1.C(OC(C1CCN(C2CCC(N)CN2)CC1)=O)C>>[CH2:36]([O:38][C:39]([CH:41]1[CH2:46][CH2:45][N:44]([C:47]2[N:9]=[CH:51][C:50]([NH:53][C:54]([C:56]3[N:57]=[C:58]([C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)[O:59][C:60]=3[C:61]([F:62])([F:64])[F:63])=[O:55])=[CH:49][N:48]=2)[CH2:43][CH2:42]1)=[O:40])[CH3:37]

Participants

5

Reactant 4

HCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 576521271-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid ethyl esterHCID 67428037HCID 67428037, compoundHCID 686370461-(5-Amino-piperidin-2-yl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 576520441-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyrimidin-2-yl}-piperidine-4-carboxylic acid ethyl ester

Procedure

With a method similar to that used for the preparation of 1-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-4-carboxylic acid ethyl ester above, 1-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-piperidin-2-yl}-piperidine-4-carboxylic acid ethyl ester was prepared from 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (1.2 equivalents) and 1-(5-amino-piperidin-2-yl)-piperidine-4-carboxylic acid ethyl ester. HRMS calcd for C23H22F3N5O4 (M+H) 490.1697, obsd 490.1695.

Sources & evidence

ORD record
ord-8ba21527c6f14cf9a2927c588d30b828
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

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