Triethylamine → HCID 59333687、化合物

HRID 1876617ノート

反応式

HRID 1876617 の反応式
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

参加物

8

反応物 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

生成物 1

HCID 59333687HCID 59333687、化合物収率 88.2%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒2 回HCID 21226129Dichloromethane methanol溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d57b32f8606545679b37f01077551514
出典データセット
uspto-grants-2012_11
特許番号
US08309546B2

反応ノート

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