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Hydrochloric Acid → 6-Acetyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-indole

HRID 1934632
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HRID 1934632 반응식
[CH3:1][Mg]Br.CON(C)[C:7]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:19]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[C:20]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])=[O:21])=[CH:14][N:15]2[CH3:18])=[CH:11][CH:10]=1)=[O:8].Cl>C(OCC)C.O1CCCC1>[C:7]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:19]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[C:20]([NH:22][S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)(=[O:24])=[O:25])=[O:21])=[CH:14][N:15]2[CH3:18])=[CH:11][CH:10]=1)(=[O:8])[CH3:1]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 22467206N6-methoxy-N6,1-dimethyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 224672486-Acetyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-indole

시약·촉매·용매 2

HCID 3283
Diethyl Ether
용매
HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

Methylmagnesium bromide (0.23 ml of a 3M solution in diethyl ether) was added dropwise to a stirred solution of N6-methoxy-N6,1-dimethyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamide (from Example 103, 174 mg, 0.32 mmol) in anhydrous tetrahydrofuran (5 ml) at −70° C. under a nitrogen atmosphere. The mixture was stirred at −70° C. for an additional 2 hours before warming to room temperature. Aqueous hydrochloric acid (5 ml of 1M solution) was slowly added to the mixture, and then it was extracted with ethyl acetate (100 ml). The organic phase was separated and washed with brine, dried (magnesium sulphate) and the solvent were removed in vacuo. The residue was flash chromatographed using a gradient elution of a mixture of 90% hexane and 10% ethyl acetate, through to 100% ethyl acetate, to give the title compound (18 mg).

후처리

  1. temperaturebefore warming to room temperature
  2. extractionit was extracted with ethyl acetate (100 ml)
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (magnesium sulphate)
  6. customthe solvent were removed in vacuo
  7. customchromatographed
  8. washa gradient elution of a mixture of 90% hexane and 10% ethyl acetate

출처 및 근거

ORD 기록
ord-f9e5bd917cd04c7a8488825107506c02
출처 데이터셋
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06384070B2

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