Triethylamine → HCID 59333687, 화합물

HRID 1876617노트

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HRID 1876617 반응식
C(N(CC)CC)C.[CH3:8][C@H:9]1[NH:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([CH2:37][C:38]([F:41])([F:40])[F:39])[C:17]3[C:22]([N:23]=2)=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:20]=[C:19]([C:30]2[CH:31]=[N:32][C:33]([NH2:36])=[N:34][CH:35]=2)[N:18]=3)[CH2:10]1.C([O:45][CH2:46][C:47](Cl)=[O:48])(=O)C.C[O-].[Na+].CO>C(Cl)Cl.CO.O1CCCC1.C(Cl)Cl.CO>[NH2:36][C:33]1[N:34]=[CH:35][C:30]([C:19]2[N:18]=[C:17]3[C:22]([N:23]=[C:15]([N:11]4[CH2:12][CH2:13][N:14]([C:46](=[O:45])[CH2:47][OH:48])[C@H:9]([CH3:8])[CH2:10]4)[N:16]3[CH2:37][C:38]([F:41])([F:39])[F:40])=[C:21]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[N:20]=2)=[CH:31][N:32]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 23694274Sodium methanolate methanolHCID 593335845-{8-[(3R)-3-Methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine

생성물 1

HCID 59333687HCID 59333687, 화합물수율 88.2%

시약·촉매·용매 3

HCID 6344Dichloromethane용매2회HCID 21226129Dichloromethane methanol용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

Triethylamine (55.9 μl, 0.40 mmol) was added to a methylene chloride suspension (3.0 ml) of 5-{8-[(3R)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine (87.2 mg, 0.18 mmol) at room temperature followed by the addition of acetoxyacetyl chloride (24.2 μl, 0.22 mmol) with ice cooling. The resulting mixture was stirred at room temperature for 1 hour, then the reaction mixture was poured into methylene chloride-methanol (10:1), washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, a 25% by weight sodium methoxide-methanol solution (83.3 μl, 0.36 mmol) was added to a methanol-tetrahydrofuran (1:1) mixture solution (12.0 ml) of the resulting white solid, and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into methylene chloride and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1) to give the title compound (85.2 mg, 87%) as a pale yellow solid.

후처리

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. stirringthe resulting mixture was stirred at room temperature for 24 hours
  6. washwashed with saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationthe mixture was filtrated
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customthe resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1)

출처 및 근거

ORD 기록
ord-d57b32f8606545679b37f01077551514
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309546B2

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