4-Methylmorpholine → HCID 178448373、化合物

HRID 1068878ノート

反応式

HRID 1068878 の反応式
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

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 178509242HCID 178509242、化合物

生成物 1

HCID 178448373HCID 178448373、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-39901dd3ce8b4193ba5101356d091ad0
出典データセット
uspto-grants-2001_06
特許番号
US06251911B1

反応ノート

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