Isopropenyl chloroformate → methyl-{5'-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl}-carbamic acid isopropenyl ester

HRID 1641843Notes

Reaction equation

HRID 1641843 reaction equation
C(OC(N1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[N:23]=[C:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:25][C:26]=3[C:27]([F:30])([F:29])[F:28])=[O:21])=[CH:15][N:14]=2)[CH2:9]C1)=O)(C)C.[C:37]([O:40][C:41](=[O:74])[N:42]([CH3:73])[CH:43]1[CH2:48]CCCN1C1C=CC(NC(C2N=C(C3C=CC=CC=3)OC=2C(F)(F)F)=O)=CN=1)([CH3:39])=[CH2:38].FC(F)(F)C(O)=O.CNC1CCN(C2C=CC(NC(C3N=C(C4C=CC=CC=4)OC=3C(F)(F)F)=O)=CN=2)CC1.ClC(OC(C)=C)=O>>[C:37]([O:40][C:41](=[O:74])[N:42]([CH3:73])[CH:43]1[CH2:48][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[N:23]=[C:24]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[O:25][C:26]=3[C:27]([F:28])([F:30])[F:29])=[O:21])=[CH:15][N:14]=2)[CH2:11][CH2:12]1)([CH3:39])=[CH2:38]

Participants

5

Reactant 4

HCID 93846Isopropenyl chloroformateHCID 576520844-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid isopropyl esterHCID 66738582methyl-{5'-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-yl}-carbamic acid isopropenyl esterHCID 866322742-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-methylamino-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-yl)-amide trifluoroacetate

Product 1

HCID 57652046methyl-{5'-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl}-carbamic acid isopropenyl 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 isopropyl ester above, methyl-{5′-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-yl}-carbamic acid isopropenyl ester was prepared from 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-methylamino-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl)-amide trifluoroacetate and isopropenyl chloroformate. LCMS calcd for C26H26F3N5O4 (m/e) 529, obsd 530 (M+H).

Sources & evidence

ORD record
ord-35fee9d5efe3458b97725c651fcb5dfb
Source dataset
uspto-grants-2012_02
Patent number
US08115011B2

Reaction notes

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