Diisopropylethylamine → 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-N,2-di-ethylbenzamide

HRID 1037012노트

반응식

HRID 1037012 반응식
[CH3:1][C:2]1([CH3:15])[O:6][B:5]([OH:7])[C:4]2[CH:8]=C(CNC)[CH:10]=[CH:11][C:3]1=2.[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2([C:39]([F:42])([F:41])[F:40])[O:28][N:27]=[C:26]([C:29]3[CH:37]=[CH:36][C:32]([C:33]([OH:35])=O)=[C:31]([CH3:38])[CH:30]=3)[CH2:25]2)[CH:20]=[C:21]([Cl:23])[CH:22]=1.F[B-](F)(F)F.Br[C:49]1C=CC=C[N+]=1CC.CC[N:59]([CH:63]([CH3:65])C)[CH:60]([CH3:62])C>C(Cl)Cl.O>[Cl:23][C:21]1[CH:20]=[C:19]([C:24]2([C:39]([F:42])([F:40])[F:41])[O:28][N:27]=[C:26]([C:29]3[CH:37]=[CH:36][C:32]([C:33]([N:59]([CH2:60][C:62]4[CH:10]=[CH:11][C:3]5[C:2]([CH3:15])([CH3:1])[O:6][B:5]([OH:7])[C:4]=5[CH:8]=4)[CH2:63][CH3:65])=[O:35])=[C:31]([CH2:38][CH3:49])[CH:30]=3)[CH2:25]2)[CH:18]=[C:17]([Cl:16])[CH:22]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 27363002-Bromo-1-ethylpyridinium tetrafluoroborateHCID 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acidHCID 866854591,3-dihydro-1-hydroxy-N,3,3-trimethyl-2,1-Benzoxaborole-6-methanamine

생성물 1

HCID 866854614-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-N,2-di-ethylbenzamide수율 11.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a cold solution of 3,3-dimethyl-6-((methylamino)methyl)benzo[c][1,2]-oxaborol-1(3H)-ol (246 mg, 1.2 mmol), 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (502 mg, 1.2 mmol) and 2-bromo-1-ethylpyridinium tetrafluoroborate (BEP) (292 mg, 1.32 mmol) in DCM (10 mL) was added DIPEA (464 mg, 3.6 mmol). The reaction mixture was stirred at rt overnight. Water (20 mL) was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC to give 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-N,2-di-ethylbenzamide (84 mg; yield 11.6%) as a white solid. HPLC purity: 98.30% at 220 nm and 98.87% at 254 nm; MS: m/z=604.9 (M+1, ESI+).

후처리

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-9044aeddc48849fc82fb9768e7b7a804
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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