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1,2-Dichloroethane → HCID 59403492、化合物

HRID 1514210
ノート
印刷プレビュー

反応式

HRID 1514210 の反応式
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.O[NH:35][C:36](=[NH:55])[C:37]1[CH:54]=[CH:53][C:40]2[CH2:41][CH2:42][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:44][CH2:45][C:39]=2[CH:38]=1>CN(C=O)C>[F:18][C:2]([F:1])([F:19])[C:3]1[CH:8]=[C:7]([C:9]2[O:11][N:35]=[C:36]([C:37]3[CH:54]=[CH:53][C:40]4[CH2:41][CH2:42][N:43]([C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])[CH2:44][CH2:45][C:39]=4[CH:38]=3)[N:55]=2)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 463151912-(Trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 178451593HCID 178451593、化合物

生成物 1

HCID 59403492HCID 59403492、化合物収率 64.5%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

2-(Trifluoromethyl)-4-biphenylcarboxylic acid (Preparation 40) (284 mg, 1.07 mmol), HOBT (159 mg, 1.18 mmol) and EDC (225 mg, 1.18 mmol) were stirred in DMF (10 ml) under argon for 20 minutes. 1,1-Dimethylethyl 7-[(hydroxyamino)(imino)methyl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 41) (326 mg, 1.07 mmol) was added and the mixture stirred at room temperature for 2.5 h before it was heated to 80° C. for 16 h. The reaction mixture was partitioned between EtOAc (30 ml) and water (30 ml) and the organic layer washed with aqueous sodium bicarbonate and water before it was dried (phase separator) and evaporated. The residue was triturated with methanol to give the title compound as a white solid (370 mg, 0.69 mmol). The filtrate was purified by Biotage Horizon, reverse phase cartridge, eluting with 5-100% acetonitrile in water to give further title compound (70 mg, 0.13 mmol). δH (d6DMSO, 400 MHz): 8.52 (1H, s), 8.50 (1H, d), 7.93 (1H, s), 7.90 (1H, dd), 7.74 (1H, d) 7.56-7.48 (3H, m), 7.41-7.38 (3H, m), 3.55-3.47 (4H, m), 3.02-2.93 (4H, m), 1.41 (9H, s).

後処理

  1. temperaturewas heated to 80° C. for 16 h
  2. customThe reaction mixture was partitioned between EtOAc (30 ml) and water (30 ml)
  3. washthe organic layer washed with aqueous sodium bicarbonate and water before it
  4. customwas dried (phase separator)
  5. customevaporated
  6. customThe residue was triturated with methanol

出典と根拠

ORDレコード
ord-8456e963a2474bbba1f11517fd4b77ab
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08222245B2

反応ノート

読み込み中…

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