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Triethylamine → Thiophene-2-carboxylic acid N'-[3-(2',3'-dimethyl-biphenyl-2-yl)-propionyl]-N'-isopropyl-hydrazide

HRID 1724155
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HRID 1724155 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17](O)=[O:18].[CH:20]([NH:23][NH:24][C:25]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)=[O:26])([CH3:22])[CH3:21].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([N:23]([CH:20]([CH3:22])[CH3:21])[NH:24][C:25]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)=[O:26])=[O:18]
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 575601053-(2',3'-Dimethyl-biphenyl-2-yl)-propionic acidHCID 596421662-Thiophenecarboxylic acid, 2-(1-methylethyl)hydrazide

생성물 1

HCID 57560107
Thiophene-2-carboxylic acid N'-[3-(2',3'-dimethyl-biphenyl-2-yl)-propionyl]-N'-isopropyl-hydrazide
수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-(2′,3′-dimethyl-biphenyl-2-yl)-propionic acid (207 mg, 0.81 mmoles) and thiophene-2-carboxylic acid N′-isopropyl-hydrazide (150 mg, 0.81 mmoles) in DMF (8 mL) was treated with triethylamine (0.34 mL, 2.44 mmoles), HOBT (132 mg, 0.98 mmoles) and EDCI (156 mg, 0.98 mmoles) at room temperature for 48 h. The reaction mixture was partitioned between 1N HCl and dichloromethane. The organic layer was washed successively with 1N NaOH and brine, then dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-50% ethyl acetate/hexanes gradient to afford the product (173 mg, 51%). LC-MS m/e 421.46 (M+H+)

후처리

  1. customThe reaction mixture was partitioned between 1N HCl and dichloromethane
  2. washThe organic layer was washed successively with 1N NaOH and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 20-50% ethyl acetate/hexanes gradient

출처 및 근거

ORD 기록
ord-1edfbb50f66c4d5fbf9f270a53c09a72
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07485752B2

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