Sodium Bicarbonate → 6-[(4R)-4-({[3-(6-Fluoro-2-oxoquinoxalin-1(2H)-yl)propyl]amino}methyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1847087ノート

反応式

HRID 1847087 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH:14]=O)[C:7](=[O:16])[CH:6]=[N:5]2.[NH2:17][CH2:18][C@@H:19]1[CH2:23][N:22]([C:24]2[CH:25]=[CH:26][C:27]3[O:28][CH2:29][C:30](=[O:34])[NH:31][C:32]=3[N:33]=2)[C:21](=[O:35])[CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][NH:17][CH2:18][C@@H:19]1[CH2:23][N:22]([C:24]3[CH:25]=[CH:26][C:27]4[O:28][CH2:29][C:30](=[O:34])[NH:31][C:32]=4[N:33]=3)[C:21](=[O:35])[CH2:20]1)[C:7](=[O:16])[CH:6]=[N:5]2

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867249736-[(4R)-4-(Aminomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneHCID 867250113-(6-fluoro-2-oxoquinoxalin-1(2H)-yl)propanal

生成物 1

HCID 867250106-[(4R)-4-({[3-(6-Fluoro-2-oxoquinoxalin-1(2H)-yl)propyl]amino}methyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-(6-fluoro-2-oxoquinoxalin-1(2H)-yl)propanal (0.1 g, 0.45 mmol), 6-[(4R)-4-(aminomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Reference Examples 54, 0.11 g, 0.45 mmol) DMF (3 ml) and molecular sieve (4 A, 0.1 g) was stirred at room temperature for 20 minutes. The reaction mixture was cooled on ice and sodium triacetoxyborohydride (0.12 g, 0.54 mmol) was gradually added thereto. Then, the mixture was stirred at room temperature for 4 hours, a sodium hydrogen carbonate aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The obtained crude product was purified by thin layer chromatography (dichloromethane/methanol) to yield the title compound. 8 mg (2%).

後処理

  1. additionwas gradually added
  2. stirringThen, the mixture was stirred at room temperature for 4 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe obtained crude product
  5. customwas purified by thin layer chromatography (dichloromethane/methanol)

出典と根拠

ORDレコード
ord-f2ba8547e75844bb92f6d29d7a0d555b
出典データセット
uspto-grants-2015_02
特許番号
US08952010B2

反応ノート

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