Ammonia → 3-Benzenesulphonyl-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine

HRID 636456노트

반응식

HRID 636456 반응식
[NH3:1].[C:2]1([S:8]([C:11]2[C:12]([S:28][CH3:29])=[N:13][N:14]3[C:19](Cl)=[CH:18][C:17]([CH2:21][N:22]4[CH2:27][CH2:26]O[CH2:24][CH2:23]4)=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:31]([CH:33]=O)C>CO>[C:2]1([S:8]([C:11]2[C:12]([S:28][CH3:29])=[N:13][N:14]3[C:19]([NH2:1])=[CH:18][C:17]([CH2:21][N:22]4[CH2:27][CH2:26][N:31]([CH3:33])[CH2:24][CH2:23]4)=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 212549113-Benzenesulphonyl-7-chloro-2-methylsulphanyl-5-morpholin-4-ylmethyl-pyrazolo[1,5-a]pyrimidine

생성물 1

HCID 212550223-Benzenesulphonyl-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine수율 83%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

10 ml of a 50% solution of NH3 in MeOH were added to a solution of 0.9 g (2 mmol) of 3-benzenesulphonyl-7-chloro-2-methylsulphanyl-5-morpholin-4-ylmethyl-pyrazolo[1,5-a]pyrimidine in 20 DMF and stirred at RT for 4 hrs. The DMF was evaporated in a high vacuum and the residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2 and the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (silica gel, CH2Cl2/MeOH/NH4OH 80:10:1) and crystallization from EtOH yielded 0.70 g (83%) of 3-benzenesulphonyl-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine as colorless crystals, m.p. 224-226°.

후처리

  1. customThe DMF was evaporated in a high vacuum
  2. customthe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with CH2Cl2
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (silica gel, CH2Cl2/MeOH/NH4OH 80:10:1) and crystallization from EtOH

출처 및 근거

ORD 기록
ord-d072ac4471944b73b435aef01598b678
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194410B1

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