Methylamine → N2-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N2-dimethylglycinamide

HRID 1668405ノート

反応式

HRID 1668405 の反応式
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:34]=[CH:33][C:25]([CH2:26][N:27]([CH3:32])[CH2:28][C:29](O)=[O:30])=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.CN.[CH2:37]([N:39](CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>O1CCCC1.C(OCC)(=O)C.C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([CH2:26][N:27]([CH3:32])[CH2:28][C:29]([NH:39][CH3:37])=[O:30])=[CH:33][CH:34]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:8][CH:9]=1

参加物

8

反応物 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 67360373N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylglycine dihydrochloride

生成物 1

HCID 59239837N2-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,N2-dimethylglycinamide収率 22.5%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of the compound (70 mg) obtained in Example 30, 2N methylamine in tetrahydrofuran solution (0.65 ml), triethylamine (59 mg), bis(2-oxo-3-oxazolidinyl)phosphinoyl chloride (39 mg) and methylene chloride (5 ml) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated is under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (10:1, volume ratio)] and recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (14 mg) as a colorless powder.

後処理

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (10:1, volume ratio)]
  5. customrecrystallized from ethyl acetate-hexane (1:1, volume ratio)

出典と根拠

ORDレコード
ord-3166cb4fe9ba44f7a45eaa8170f60c8f
出典データセット
uspto-grants-2011_08
特許番号
US07989445B2

反応ノート

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