Dabco → 6-{3-Chloro-4-[2-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-4-trifluoromethyl-nicotinic acid methyl ester

HRID 2386773Notes

Reaction equation

HRID 2386773 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:29])[C:10]([C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[N:21]([CH2:26][CH3:27])[C:20]=2[CH:28]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[CH3:30][O:31][C:32](=[O:44])[C:33]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][C:36](Cl)=[N:35][CH:34]=1.C1N2CCN(CC2)C1>>[CH3:30][O:31][C:32](=[O:44])[C:33]1[C:38]([C:39]([F:40])([F:41])[F:42])=[CH:37][C:36]([O:8][C:6]2[CH:5]=[CH:4][C:3]([CH:9]([CH3:29])[C:10]([C:16]3[CH:17]=[CH:18][C:19]4[O:24][CH2:23][C:22](=[O:25])[N:21]([CH2:26][CH3:27])[C:20]=4[CH:28]=3)([OH:15])[C:11]([F:12])([F:13])[F:14])=[C:2]([Cl:1])[CH:7]=2)=[N:35][CH:34]=1

Participants

4

Reactant 3

HCID 9237DabcoHCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinateHCID 666973516-[2-(2-Chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 866458746-{3-Chloro-4-[2-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-4-trifluoromethyl-nicotinic acid methyl ester

Procedure

In analogy to Example 62, step 1, 6-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one (Example 64, step 5) was reacted with methyl-6-chloro-4-(trifluoromethyl)nicotinate and DABCO to give the title compound as a white solid. MS (m/e)=633.4 [M+H+].

Sources & evidence

ORD record
ord-04d462d64fee4c059030e46b1a4a9e5f
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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