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 1037012ノート

反応式

HRID 1037012 の反応式
[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

参加物

7

反応物 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

生成物 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-ethylbenzamide収率 11.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-9044aeddc48849fc82fb9768e7b7a804
出典データセット
uspto-grants-2013_10
特許番号
US08546357B2

反応ノート

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