Methyl 4-cyano-3-phenylisothiazole-5-carboxylate → 3-Phenyl-5-(7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)isothiazole-4-carbonitrile

HRID 1506518Notes

Reaction equation

HRID 1506518 reaction equation
C1(N2C(C(F)(F)F)=C(C3ON=C4C5C(CCC=34)=CC(C=C)=CC=5)C=N2)C=CC=CC=1.[CH:31]([C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)/[C:39](=[N:43]/[OH:44])/[CH2:38][CH2:37][CH2:36]2)=[CH2:32].[C:45]([C:47]1[C:48]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[N:49][S:50][C:51]=1[C:52](OC)=O)#[N:46]>>[C:56]1([C:48]2[C:47]([C:45]#[N:46])=[C:51]([C:52]3[O:44][N:43]=[C:39]4[C:40]5[C:35]([CH2:36][CH2:37][C:38]=34)=[CH:34][C:33]([CH:31]=[CH2:32])=[CH:42][CH:41]=5)[S:50][N:49]=2)[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Participants

4

Reactant 3

HCID 67169144Methyl 4-cyano-3-phenylisothiazole-5-carboxylateHCID 671704203-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazoleHCID 121012766(NE)-N-(6-ethenyl-3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine2×

Product 1

HCID 671700843-Phenyl-5-(7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)isothiazole-4-carbonitrile

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 1) and methyl 4-cyano-3-phenylisothiazole-5-carboxylate (Preparation 106A) 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-4c3cacf371734854b7b35eb08849fd37
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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