Acetic Acid → (R)-4-[1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl]-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl acetate

HRID 449775노트

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HRID 449775 반응식
[CH:1]1([CH:6]([N:10]2[CH:14]=[C:13]([C:15]3[C:16]4[C:25](I)=[CH:24][NH:23][C:17]=4[N:18]=[C:19]([O:21][CH3:22])[N:20]=3)[CH:12]=[N:11]2)[CH2:7][C:8]#[N:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:27]([OH:30])(=[O:29])[CH3:28]>C([O-])(=O)C.[Ag+]>[C:27]([O:30][C:25]1[C:16]2[C:15]([C:13]3[CH:12]=[N:11][N:10]([C@@H:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:7][C:8]#[N:9])[CH:14]=3)=[N:20][C:19]([O:21][CH3:22])=[N:18][C:17]=2[NH:23][CH:24]=1)(=[O:29])[CH3:28]

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 670948833-cyclopentyl-3-[4-(5-iodo-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

생성물 1

HCID 58220995(R)-4-[1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl]-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl acetate

시약·촉매·용매 1

HCID 11246Silver acetate촉매

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온도
70 °C

실험 절차

A solution of 3-cyclopentyl-3-[4-(5-iodo-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (0.25 g, 0.54 mmol) in acetic acid (3 mL) was treated with silver acetate (0.27 g, 1.6 mmol) and heated to 70° C. for 16 h. The mixture was filtered, rinsed with MeCN, water was added to the filtrate and this mixture was stirred for 20 min, Solid sodium chloride was added to this solution. The product was obtained by extraction of this aqueous mixture with three portions of ethyl acetate. The combined extracts were dried over sodium sulfate, decanted and concentrated. A portion of the product was used in the hydrolysis step (Step 4) without further purification. 1H NMR (300 MHz, CDCl3): δ 9.87 (br s, 1H), 8.39 (s, 1H), 8.37 (s, 1H), 7.33 (s, 1H), 4.22 (dt, 1H), 4.06 (s, 3H), 3.14 (dd, 1H), 2.94 (dd, 1H), 2.64-2.47 (m, 1H), 2.36 (s, 3H), 2.03-1.86 (m, 1H), 1.79-1.12 (m, 7H); LCMS (M+H)+: 395.1.

후처리

  1. filtrationThe mixture was filtered
  2. washrinsed with MeCN, water
  3. additionwas added to the filtrate
  4. additionSolid sodium chloride was added to this solution
  5. customThe product was obtained by extraction of this aqueous mixture with three portions of ethyl acetate
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. customdecanted
  8. concentrationconcentrated
  9. customA portion of the product was used in the hydrolysis step (Step 4) without further purification

출처 및 근거

ORD 기록
ord-175ad5272482495c9ab9f39a3cde6b3a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486902B2

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