Hydrochloric Acid → (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine

HRID 1969761노트

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HRID 1969761 반응식
[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=5)(=[O:22])=[O:21])[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([NH:30]C(=O)C)[CH2:4]1)[CH3:2].Cl>O1CCOCC1>[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=5)(=[O:22])=[O:21])[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([NH2:30])[CH2:4]1)[CH3:2]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 58557700N-((1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)acetamide

생성물 1

HCID 58557840(1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine수율 56%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

To a solution of N-((1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)acetamide (6.0 g, 12.86 mmol, Example #8 Step L) in 1,4-dioxane (78 mL) was added HCl (6 N aqueous, 75 mL, 450 mmol). The reaction mixture was heated at about 95° C. for about 16 h. The reaction was cooled to ambient temperature and the solvent was removed under reduced pressure. The residue was diluted with DCM (50 mL) and washed with saturated aqueous NaHCO3 (100 mL). The aqueous portion was extracted with additional DCM (3×50 mL) and the combined organic layers were dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-100% DCM/MeOH/NH4OH (950:45:5) in DCM to give (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine (3.05 g, 56%) as a tan solid: LC/MS (Table 1, Method a) Rt=1.85 min; MS m/z: 425 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was diluted with DCM (50 mL)
  4. washwashed with saturated aqueous NaHCO3 (100 mL)
  5. extractionThe aqueous portion was extracted with additional DCM (3×50 mL)
  6. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe crude material was purified by silica gel chromatography
  9. washeluting with a gradient of 0-100% DCM/MeOH/NH4OH (950:45:5) in DCM

출처 및 근거

ORD 기록
ord-f56fcc4892c4436d94cb0b11f6fcbfcf
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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