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

HRID 1037053
ノート
印刷プレビュー

反応式

HRID 1037053 の反応式
[NH2:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:12]([CH3:14])([CH3:13])[O:11][B:10]([OH:15])[C:9]=2[CH:16]=1)([CH3:4])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:50][C:51]1[CH:59]=[C:58]([C:60]2[CH2:64][C:63]([C:69]3[CH:74]=[C:73]([Cl:75])[C:72]([Cl:76])=[C:71]([Cl:77])[CH:70]=3)([C:65]([F:68])([F:67])[F:66])[O:62][N:61]=2)[CH:57]=[CH:56][C:52]=1[C:53](O)=[O:54]>C1COCC1.CC(=O)OCC>[OH:15][B:10]1[C:9]2[CH:16]=[C:5]([C:2]([NH:1][C:53](=[O:54])[C:52]3[CH:56]=[CH:57][C:58]([C:60]4[CH2:64][C:63]([C:69]5[CH:74]=[C:73]([Cl:75])[C:72]([Cl:76])=[C:71]([Cl:77])[CH:70]=5)([C:65]([F:68])([F:67])[F:66])[O:62][N:61]=4)=[CH:59][C:51]=3[CH3:50])([CH3:4])[CH3:3])[CH:6]=[CH:7][C:8]=2[C:12]([CH3:14])([CH3:13])[O:11]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866854502-Methyl-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzoic acidHCID 866854976-(2-aminopropan-2-yl)-3,3-dimethylbenzo[c][1,2]-oxaborol-1(3H)-ol

生成物 1

HCID 71576286
N-(2-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)propan-2-yl)-2-methyl-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzamide
収率 41.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-(2-aminopropan-2-yl)-3,3-dimethylbenzo[c][1,2]-oxaborol-1(3H)-ol (100 mg), HATU (277 mg, 0.73 mmol) and DIPEA (0.2 mL, 1.1 mmol) in THF (5 mL) was added 2-methyl-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzoic acid (80 mg, 0.37 mmol). The reaction mixture was stirred at rt overnight. EA was added and the mixture was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC to give the final title compound N-(2-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)propan-2-yl)-2-methyl-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzamide (100 mg; yield 38% over 3 steps) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.99 (s, 1H), 8.64 (s, 1H), 7.85 (s, 2H), 7.74 (s, 1H), 7.47-7.55 (m, 4H), 7.36 (d, J=8.4 Hz, 1H), 4.41 (d, J=18.4 Hz, 1H), 4.34 (d, J=18.4 Hz, 1H), 2.33 (s, 3H), 1.66 (s, 6H), 1.44 (s, 6H) ppm; HPLC purity: 99.29% at 220 nm and 99.63% at 254 nm; MS: m/z=653.8 (M+1, ESI+).

後処理

  1. washthe mixture was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-0f98f6a1ae2e4a729cd613c0185d25de
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546357B2

反応ノート

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