Formaldehyde → N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-2-nitrobenzamide

HRID 77379

反応式

HRID 77379 の反応式
[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][N:2]1[C:9]1[CH:10]=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[C:13]([CH:18]=1)[C:14]([NH:16][CH3:17])=[O:15].C=O.[C:24]([BH3-])#N>C(#N)C.C(O)(=O)C>[CH3:17][NH:16][C:14](=[O:15])[C:13]1[CH:18]=[C:9]([N:2]2[CH2:3][CH:4]3[CH:5]([CH2:6][N:7]([CH3:24])[CH2:8]3)[CH2:1]2)[CH:10]=[CH:11][C:12]=1[N+:19]([O-:21])=[O:20]

参加物

6

反応物 3

HCID 712FormaldehydeHCID 498716Cyano-borohydrideHCID 699287575-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-methyl-2-nitrobenzamide2 回

生成物 1

HCID 69929569N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-2-nitrobenzamide収率 48.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 6342Acetonitrile溶媒

反応条件

温度
130 °C

実験手順

5-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-methyl-2-nitrobenzamide (1.78 g, 6.13 mmol) (Intermediate 10B) was dissolved in acetonitrile (45 mL) before addition of formaldehyde (0.6 g, 7.36 mmol) and MP-cyanoborohydride (3.6 g, 9.25 mmol) followed by 6 drops of acetic acid. The resulting mixture was split into 3 microwave vials and heated at 130° C. for 20 minutes. The reaction mixture was filtered and concentrated. The resultant crude material was purified by a 50 g silica column in 100% dichloromethane, 20% methanol in dichloromethane, 100% methanol (Biotage Snap cartridge). Fractions of the product were combined and reduced to dryness under reduced pressure to afford N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-2-nitrobenzamide (900 mg, 2.96 mmol).

後処理

  1. customThe resulting mixture was split into 3 microwave vials
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customThe resultant crude material was purified by a 50 g silica column in 100% dichloromethane

出典と根拠

ORDレコード
ord-17f24f06fe374049899ae91f4f06fed1
出典データセット
uspto-grants-2014_09
特許番号
US08841289B2

関連ノート

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