Acetic Acid → (S)-(1-(6-methyl-2-(methyl(4-(2-methyl-1H-imidazol-1-yl)phenyl)amino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol

HRID 1930641ノート

反応式

HRID 1930641 の反応式
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([N:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][C@H:25]4CO)[C:17]4[CH2:23][NH:22][CH2:21]C[C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[C:35](O)(=O)[CH3:36].[CH2:39]=[O:40].[C:41]([BH3-])#N.[Na+]>CO>[CH3:21][N:22]1[CH2:36][CH2:35][C:18]2[N:19]=[C:14]([N:13]([CH3:41])[C:10]3[CH:9]=[CH:8][C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[CH3:1])=[CH:12][CH:11]=3)[N:15]=[C:16]([N:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][C@H:25]3[CH2:39][OH:40])[C:17]=2[CH2:23]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333741(S)-(1-(2-(4-(2-Methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol

生成物 1

HCID 46199433(S)-(1-(6-methyl-2-(methyl(4-(2-methyl-1H-imidazol-1-yl)phenyl)amino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol収率 27.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(S)-(1-(2-(4-(2-Methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol (49 mg, 0.11 mmol) was dissolved in methanol (3 mL). Acetic acid (6.18 μL, 0.11 mmol) was added followed by formaldehyde (0.016 mL, 0.22 mmol). The reaction mixture was allowed to stirred at room temperature for 15 minutes and sodium cyanoborohydride (13.58 mg, 0.22 mmol) was added. After 1 h the solvent was evaporated and the crude dissolved in few drops of methanol, filtered and purified by preparative HPLC to give (S)-(1-(6-methyl-2-(methyl(4-(2-methyl-1H-imidazol-1-yl)phenyl)amino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol (14.80 mg, 26.2%) and (S)-(1-(6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)indolin-2-yl)methanol (4.60 mg, 8.07%) were obtained as acetate salt.

後処理

  1. customAfter 1 h the solvent was evaporated
  2. dissolutionthe crude dissolved in few drops of methanol
  3. filtrationfiltered
  4. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-02a6b51ab5cd46479b95c5a24a549bba
出典データセット
uspto-grants-2012_05
特許番号
US08188101B2

反応ノート

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