Acetic Acid → 3-(cyclopropyl(6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)propanenitrile

HRID 1930657ノート

反応式

HRID 1930657 の反応式
[CH:1]1([N:4]([C:9]2[C:10]3[CH2:31][NH:30][CH2:29][CH2:28][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][N:24]=[C:23]4[CH3:27])=[CH:18][CH:17]=3)[N:14]=2)[CH2:5][CH2:6][C:7]#[N:8])[CH2:3][CH2:2]1.[C:32](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH:1]1([N:4]([C:9]2[C:10]3[CH2:31][N:30]([CH3:32])[CH2:29][CH2:28][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][N:24]=[C:23]4[CH3:27])=[CH:18][CH:17]=3)[N:14]=2)[CH2:5][CH2:6][C:7]#[N:8])[CH2:2][CH2:3]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 593337983-(Cyclopropyl(2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)propanenitrile

生成物 1

HCID 461995873-(cyclopropyl(6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)propanenitrile収率 3.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3-(Cyclopropyl(2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)propanenitrile (94 mg, 0.23 mmol) was dissolved in methanol (2 mL). Acetic acid (0.013 mL, 0.23 mmol) was added followed by formaldehyde (0.017 mL, 0.23 mmol). The reaction mixture was stirred at room s temperature for 15 minutes and sodium cyanoborohydride (14.25 mg, 0.23 mmol) was added. The reaction mixture was concentrated under reduced pressure, filtered and purified by preparative HPLC (acidic system) yielding 3-(cyclopropyl(6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)propanenitrile (3.50 mg, 3.16%) as acetate salt.

後処理

  1. customfor 15 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationfiltered
  4. custompurified by preparative HPLC (acidic system)

出典と根拠

ORDレコード
ord-b3964615914a4f41977058e942c117d5
出典データセット
uspto-grants-2012_05
特許番号
US08188101B2

反応ノート

読み込み中…