Hydrochloric Acid → 2-Hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

HRID 2204573노트

반응식

HRID 2204573 반응식
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([NH:20][NH:21]C(OC(C)(C)C)=O)[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].S(N1C2=NC=C(N(C(OC(C)(C)C)=O)N)N=C2C=C1)(C1C=CC(C)=CC=1)(=O)=O.Cl>O1CCOCC1>[NH:20]([C:18]1[N:19]=[C:14]2[CH:13]=[CH:12][N:11]([S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:2])=[O:3])[C:15]2=[N:16][CH:17]=1)[NH2:21]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 58009788HCID 58009788, 화합물HCID 580099261,1-Dimethylethyl 2-[5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]hydrazinecarboxylate

생성물 1

HCID 580098102-Hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine수율 50%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

To a mixture of tert-butyl 2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate and tert-butyl 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate (18.8 g, 46.6 mmol) in 1,4-dioxane (239 mL) was added HCl (4 M in 1,4-dioxane, 86 mL, 345 mmol). The reaction was heated at about 60° C. for about 1 h and then cooled to about 15-20° C. The solid was collected by vacuum filtration, washed with cold 1,4-dioxane (2×20 mL), and then stirred with a solution of saturated aqueous NaHCO3 and water (1:1, 150 mL). After about 1 h, the effervescence had subsided and the solid was collected by vacuum filtration, washed with ice cold water (3×20 mL), and dried in a vacuum oven to a constant weight to afford 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine as a light yellowish brown solid (8.01 g, 50%): LC/MS (Table 2, Method d) Rt=1.28 min; MS m/z: 304 (M+H)+.

후처리

  1. temperaturecooled to about 15-20° C
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with cold 1,4-dioxane (2×20 mL)
  4. filtrationthe solid was collected by vacuum filtration
  5. washwashed with ice cold water (3×20 mL)
  6. customdried in a vacuum oven to a constant weight

출처 및 근거

ORD 기록
ord-11a4bad4517e4e2a9dd6963fde7ad3b2
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365579B2

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