1,2-Dichloroethane → ethyl 3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isopropyl)amino)cyclobutyl)propanoate

HRID 2040619

반응식

HRID 2040619 반응식
[CH3:1][O:2][C:3]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@H:23]4[C@H:19]([O:20][C:21]([CH3:25])([CH3:24])[O:22]4)[C@@H:18]([CH2:26][NH:27][CH:28]([CH3:30])[CH3:29])[CH2:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1.ClCCCl.O=[C:42]1[CH2:45][CH:44]([CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@@H:23]4[O:22][C:21]([CH3:24])([CH3:25])[O:20][C@@H:19]4[C@@H:18]([CH2:26][N:27]([CH:28]([CH3:30])[CH3:29])[CH:42]4[CH2:45][CH:44]([CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43]4)[CH2:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 67775333Ethyl 3-(3-oxocyclobutyl)propanoateHCID 67775374N-(2,4-dimethoxybenzyl)-7-((3aS,4R,6R,6aR)-6-((isopropylamino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 67777277ethyl 3-(3-((((3aR,4R,6R,6aS)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(isopropyl)amino)cyclobutyl)propanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-(2,4-dimethoxybenzyl)-7-((3aS,4R,6R,6aR)-6-((isopropylamino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (9.50 g, 15.3 mmol) in 1,2-Dichloroethane (75 mL, 950 mmol) was treated with ethyl 3-(3-oxocyclobutyl)propanoate (3.92 g, 23.0 mmol) and Acetic acid (1.0 mL, 18 mmol;) dropwise followed by Sodium triacetoxyborohydride (4.58 g, 21.6 mmol) and the mixture was stirred at RT for 6 days. The reaction mixture was diluted with 150 mL CH2Cl2 and washed with 100 mL sat NaHCO3. The aqueous phase was washed with 100 mL CH2Cl2 and the combined organic phase was dried over Na2SO4, filtered and concentrated to yield a light brown viscous glass.

후처리

  1. washwashed with 100 mL
  2. washThe aqueous phase was washed with 100 mL CH2Cl2
  3. dry with materialthe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a light brown viscous glass

출처 및 근거

ORD 기록
ord-a36842ef8b134e21a585afeca22acc2a
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580762B2

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