4-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid → 4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-2-methylbenzamide

HRID 1037009Notes

Reaction equation

HRID 1037009 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:28][CH2:29][C:30]1[CH:31]=[CH:32][C:33]2[CH2:37][O:36][B:35]([OH:38])[C:34]=2[CH:39]=1.ClC1C=C(C2(C(F)(F)F)ON=C(C3C=CC(C(NC4C=CC5COB(O)C=5C=4)=O)=C(C)C=3)C2)C=C(Cl)C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:25])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:28][CH2:29][C:30]4[CH:31]=[CH:32][C:33]5[CH2:37][O:36][B:35]([OH:38])[C:34]=5[CH:39]=4)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 3

HCID 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acidHCID 682815336-(aminomethyl)benzo[c][1,2]oxaborol-1(3H)-olHCID 866854544-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-methylbenzamide

Product 1

HCID 715758834-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-2-methylbenzamide

Procedure

The title compound was prepared from 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid and 6-(aminomethyl)benzo[c][1,2]oxaborol-1(3H)-ol by the same method as described for 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-methylbenzamide. It was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.21 (s, 1 H), 8.94 (m, 1 H), 7.37-7.82 (m, 9 H), 4.95 (s, 2 H), 4.49 (m, 2 H), 4.34 (m, 2 H), 2.37 (s, 3 H) ppm; MS: m/z=563 (M+1, ESI+).

Workup

  1. customIt was obtained as a white solid

Sources & evidence

ORD record
ord-65aa1ea689fc4374a0718d03f6b29f50
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

Loading…