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

HRID 1037029ノート

反応式

HRID 1037029 の反応式
[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]([OH:20])=O)=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:62][CH2:63][C:64]1[CH:65]=[CH:66][C:67]2[C:71]([CH2:74][F:75])([CH2:72][F:73])[O:70][B:69]([OH:76])[C:68]=2[CH:77]=1>CN(C=O)C>[F:75][CH2:74][C:71]1([CH2:72][F:73])[O:70][B:69]([OH:76])[C:68]2[CH:77]=[C:64]([CH2:63][NH:62][C:18](=[O:20])[C:17]3[CH:21]=[CH:22][C:14]([C:11]4[CH2:10][C:9]([C:4]5[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=5)([C:24]([F:27])([F:25])[F:26])[O:13][N:12]=4)=[CH:15][C:16]=3[CH3:23])[CH:65]=[CH:66][C:67]1=2

参加物

6

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 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acidHCID 866854756-(aminomethyl)-3,3-bis(fluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol hydrochloride

生成物 1

HCID 71576076N-((3,3-bis(fluoromethyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-benzamide収率 33.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-benzoic acid (100 mg, 0.24 mmol) and DIPEA (124 mg, 0.88 mmol) in DMF (5 mL) was stirred at rt for 5 min and then HATU (183 mg, 0.48 mmol) was added. The mixture was stirred for 10 min prior to the addition of 6-(aminomethyl)-3,3-bis(fluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (126 mg, 0.44 mmol). And the resulting mixture was stirred at rt overnight. It was then concentrated under vacuum, and the residue was partitioned between 1N HCl and ethyl acetate. The organic layer separated was concentrated under vacuum, and the residue was purified by prep-TLC to provide the final title product (50 mg, 33%). 1H NMR (400 MHz, CDCl3): δ 7.47 (m, 9H), 4.61 (m, 6H), 4.07 (d, 1H), 3.78 (d, 1H), 2.41 (s, 3H) ppm; HPLC purity: 100% at 220 nm and 100% at 254 nm.

後処理

  1. stirringAnd the resulting mixture was stirred at rt overnight
  2. concentrationIt was then concentrated under vacuum
  3. customthe residue was partitioned between 1N HCl and ethyl acetate
  4. customThe organic layer separated
  5. concentrationwas concentrated under vacuum
  6. customthe residue was purified by prep-TLC

出典と根拠

ORDレコード
ord-46d49b3822a84270a0a14cc8d73cac7e
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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