Water → HCID 58406163、化合物

HRID 221613

反応式

HRID 221613 の反応式
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][O:17][CH2:16][C@H:15]([CH3:19])[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:20])[CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:27]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1.O>CN(C=O)C.C(Cl)(Cl)Cl>[N:27]1([C:32]([O:20][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([NH2:1])[C:11]2[N:12]=[C:13]4[CH2:18][O:17][CH2:16][C@H:15]([CH3:19])[N:14]4[C:10]3=2)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 709371-Pyrrolidinecarbonyl chlorideHCID 58406167(11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-2-ol

生成物 1

HCID 58406163HCID 58406163、化合物収率 17.9%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of (11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-2-ol (500 mg, 1.85 mmol) dissolved in 15 mL of DMF was treated with cesium carbonate (1.80 g, 5.55 mmol) and pyrrolidinecarbonyl chloride (275 mg, 2.03 mmol). After stirring overnight at ambient temperature, the light brown mixture was poured into 150 mL of H2O and stirred for 30 minutes. The reaction mixture was extracted with CHCl3 (3×75 mL) and the combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give a brown solid. Chromatography (SiO2, 0-20% CMA/CHCl3) gave an off-white solid which was crystallized from acetonitrile to give 122 mg of the title compound as an off-white solid, mp 218-219° C.

後処理

  1. stirringstirred for 30 minutes
  2. extractionThe reaction mixture was extracted with CHCl3 (3×75 mL)
  3. dry with materialthe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a brown solid
  7. customwas crystallized from acetonitrile

出典と根拠

ORDレコード
ord-68bc82118c8d4fbdaa40c9cdde20e58f
出典データセット
uspto-grants-2012_06
特許番号
US08207162B2

関連ノート

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