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1,2-Dichloroethane → HCID 59403492, 화합물

HRID 1514210
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HRID 1514210 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

HCID 59403492HCID 59403492, 화합물수율 64.5%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8456e963a2474bbba1f11517fd4b77ab
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222245B2

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