Formic Acid → (R)-N,N-dimethyl-2-(5-(1-methylpyrrolidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)ethanamine

HRID 241675노트

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HRID 241675 반응식
[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@@H:17]3[CH2:21][CH2:20][NH:19][CH2:18]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24].C=O.[CH:30](O)=O>O1CCOCC1>[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@@H:17]3[CH2:21][CH2:20][N:19]([CH3:30])[CH2:18]3)(=[O:15])=[O:16])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:22][C:23]([CH3:24])([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 58513585(R)-N,N-dimethyl-2-(2-neopentyl-5-(pyrrolidin-3-ylsulfonyl)-1H-benzo[d]imidazol-1-yl)ethanamine

생성물 1

HCID 46851890(R)-N,N-dimethyl-2-(5-(1-methylpyrrolidin-3-ylsulfonyl)-2-neopentyl-1H-benzo[d]imidazol-1-yl)ethanamine수율 89.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
45 °C

실험 절차

To a solution of (R)—N,N-dimethyl-2-(2-neopentyl-5-(pyrrolidin-3-ylsulfonyl)-1H-benzo[d]imidazol-1-yl)ethanamine (STEP C, 453 mg, 1.15 mmol) in 1,4-dioxane (5 mL) was added 37% formalin (343 microL, 4.27 mmol) and formic acid (221 microL, 5.77 mmol) at 0° C. The mixture was stirred at 45° C. for 1 h. The mixture was concentrated in vacuo. The residue was diluted with sodium bicarbonate aqueous solution and extracted with ethyl acetate (60 mL×2). The combined organic layers were washed with brine and dried over sodium sulfate. The resulting solution was concentrated and residue was purified by amine gel column chromatography (dichloromethane-ethyl acetate, gradient) to give the title compound (419 mg, 89%) as a clear grease.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additionThe residue was diluted with sodium bicarbonate aqueous solution
  3. extractionextracted with ethyl acetate (60 mL×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe resulting solution was concentrated
  7. customresidue was purified by amine gel column chromatography (dichloromethane-ethyl acetate, gradient)

출처 및 근거

ORD 기록
ord-e1815d40218444c8a381e93c2f516b12
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653063B2

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