Acetic Acid → HCID 59333737、化合物

HRID 1930663ノート

反応式

HRID 1930663 の反応式
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([NH:23][CH2:24][C@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[C:16]4[CH2:22][NH:21][CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.[C:30](O)(=[O:32])[CH3:31].C([BH3-])#N.[Na+]>CO>[O:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13]3[N:14]=[C:15]([NH:23][CH2:24][C@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[C:16]4[CH2:22][N:21]([CH2:31][CH2:30][OH:32])[CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:10][CH:11]=2)=[CH:4][N:3]=[CH:2]1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 67410437HCID 67410437、化合物2 回

生成物 1

HCID 59333737HCID 59333737、化合物収率 20.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(R)-N2-(4-(Oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (135 mg, 0.34 mmol) was dissolved in methanol (3 mL). Acetic acid (0.020 mL, 0.34 mmol) was added followed by (R)-N2-(4-(oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (135 mg, 0.34 mmol). The reaction mixture was stirred at room temperature for 15 minutes and sodium cyanoborohydride (21.62 mg, 0.34 mmol) (MP—CNBH3) was added and the reaction was stirred overnight. The crude was filtered, concentrated under reduced pressure, dissolved in methanol, filtered and purified by preparative HPLC yielding (R)-2-(2-(4-(oxazol-5-yl)phenylamino)-4-((tetrahydrofuran-2-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol (31.0 mg, 18.15%) as acetate salt. MS (ES+) m/z 437.3 (M+H)+;

後処理

  1. stirringthe reaction was stirred overnight
  2. filtrationThe crude was filtered
  3. concentrationconcentrated under reduced pressure
  4. dissolutiondissolved in methanol
  5. filtrationfiltered
  6. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-d8a13290e7224e6b9fc3cdd412b616f6
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…