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Triethylamine → 2-Methyl-N-(2-{[1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)propanamide

HRID 2423193
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HRID 2423193 반응식
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][NH2:22])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:34])[CH:31]([CH3:33])[CH3:32]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:32][CH:31]([CH3:33])[C:30]([NH:22][CH2:21][CH2:20][O:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[CH:11]=[CH:12]2)=[O:34]
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6

반응물 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 443895342-{[1-(Phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine2회

생성물 1

HCID 672406902-Methyl-N-(2-{[1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)propanamide수율 264.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

2-{[1-(Phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine (Intermediate 24, 0.20 g, 0.63 mmol) in DCM (100 mL) was treated with triethylamine (0.27 mL, 1.9 mmol) and 4-dimethylaminopyridine (39 mg, 0.32 mmol). The solution was cooled to 0° C. and was treated with isobutyryl chloride (0.14 g, 0.13 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was washed with saturated aqueous NaHCO3 (50 mL) and 1 M HCl (2×40 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (133 mg). MS m/z 387 [M+H]+.

후처리

  1. washThe mixture was washed with saturated aqueous NaHCO3 (50 mL) and 1 M HCl (2×40 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-95e9dd96a255415aa6c62a0daf4441c4
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960374B2

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