Acetone → N-(4-(4-(3-(isopropylamino)propanoyl)piperazin-1-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

HRID 79624노트

반응식

HRID 79624 반응식
[NH2:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][N:15]=[C:14]3[NH:24][CH:25]=[C:26]([NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=4)[C:13]=23)[CH2:8][CH2:7]1)=[O:5].[CH3:36][C:37]([CH3:39])=O.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].Cl>C(Cl)Cl.CCOCC.CO.CN(C=O)C.ClCCCl>[CH:37]([NH:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:16][N:15]=[C:14]3[NH:24][CH:25]=[C:26]([NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=4)[C:13]=23)[CH2:8][CH2:7]1)=[O:5])([CH3:39])[CH3:36]

참가 물질

12

반응물 6

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 44198253HCID 44198253, 화합물

생성물 1

HCID 44198256N-(4-(4-(3-(isopropylamino)propanoyl)piperazin-1-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide수율 7.5%

시약·촉매·용매 5

HCID 111,2-Dichloroethane용매HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

N-(4-(4-(3-Aminopropanoyl)piperazin-1-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.015 g, 0.026 mmol, see Example 65) and acetone (0.0150 g, 0.259 mmol) were placed in 1:1 DCE:DMF (2 mL). DIEA (d 0.742; 0.0226 mL, 0.130 mmol) was then added, followed by the addition of NaBH(OAc)3 (0.0110 g, 0.0518 mmol). The reaction was then stirred for 30 minutes, and poured into Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated. The residue was purified by reverse phase HPLC to give the product. The product was then dissolved in minimal DCM and MeOH and added to a stirring solution of 1M HCl in ether. The resulting solid was collected to give N-(4-(4-(3-(isopropylamino)propanoyl)piperazin-1-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.001 g, 6.2% yield) as the trihydrochloride salt. MS APCI (+) m/z 512 detected.

후처리

  1. extractionextracted into DCM
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by reverse phase HPLC
  6. customto give the product
  7. customThe resulting solid was collected

출처 및 근거

ORD 기록
ord-9e772b7f62804d71aba559675c85aea7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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