4-Methylmorpholine → HCID 178448373, 화합물

HRID 1068878노트

반응식

HRID 1068878 반응식
C[N:2]1[CH2:7][CH2:6][O:5]CC1.Cl[C:9]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10].[NH2:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[N:23][C:24]=2[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[NH:19][N:18]=1>C1COCC1>[CH2:12]([O:11][C:9]([NH:2][C@H:7]([C:6]([NH:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[N:23][C:24]=2[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[NH:19][N:18]=1)=[O:5])[CH:27]([CH3:32])[CH3:28])=[O:10])[C:13]1[CH:15]=[CH:20][CH:25]=[CH:24][CH:14]=1

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 178509242HCID 178509242, 화합물

생성물 1

HCID 178448373HCID 178448373, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Analogously to Example 5, 386 mg (1.53 mmol) of N-benzyloxycarbonyl-(D,L)valine in 3.2 ml of THF and 337 μl (3.07 mmol) of NMM are activated with 219 μl (1.68 mmol) of isobutyl chloroformate and then reacted with 400 mg (1.53 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6). The reaction mixture is concentrated by evaporation; ethyl acetate is added to the residue and the ethyl acetate suspension is washed with 2N HCl solution, sat. NaHCO3 solution and brine and finally the insoluble crude product is filtered off. Crystallization from a hot mixture of 1.1 ml of DMSO and 10 ml of ethanol yields rac.-3-([N-benzyloxycarbonyl-valyl]-amino)-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine; HPLC:tRet(grad20-100/20)=1 4.9; FAB-MS: (M+H)+=494.

후처리

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. additionethyl acetate is added to the residue
  3. washthe ethyl acetate suspension is washed with 2N HCl solution, sat. NaHCO3 solution and brine
  4. filtrationfinally the insoluble crude product is filtered off
  5. customCrystallization
  6. additionfrom a hot mixture of 1.1 ml of DMSO and 10 ml of ethanol

출처 및 근거

ORD 기록
ord-39901dd3ce8b4193ba5101356d091ad0
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251911B1

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