Methyl 5-phenyl-4-(trifluoromethyl)isothiazole-3-carboxylate → 3-(5-Phenyl-4-(trifluoromethyl)isothiazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

HRID 1506516Notes

Reaction equation

HRID 1506516 reaction equation
C1(N2C(C(F)(F)F)=C([C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]=[CH2:30])=[CH:23][CH:22]=5)C=N2)C=CC=CC=1.C(C1C=C2C(=CC=1)C(=NO)CCC2)=C.[C:45]1([C:51]2[S:55][N:54]=[C:53](C(OC)=O)[C:52]=2[C:60]([F:63])([F:62])[F:61])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[C:45]1([C:51]2[S:55][N:54]=[C:53]([C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]=[CH2:30])=[CH:23][CH:22]=5)[C:52]=2[C:60]([F:63])([F:62])[F:61])[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

4

Reactant 3

HCID 67168409Methyl 5-phenyl-4-(trifluoromethyl)isothiazole-3-carboxylateHCID 671704203-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazoleHCID 866698666-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime

Product 1

HCID 671716503-(5-Phenyl-4-(trifluoromethyl)isothiazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

Procedure

The titled compound was prepared using the experimental protocol described for Preparation 89A employing 6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime (Intermediate I-1) and methyl 5-phenyl-4-(trifluoromethyl)isothiazole-3-carboxylate (Preparation 105B) as starting materials. The compound had an HPLC retention time=4.30 min. (condition C); LC/MS M+1=424.9.

Sources & evidence

ORD record
ord-2608c901a09b4ed790312e0d80e1ce40
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…