Acetic Acid → HCID 59333737, 화합물

HRID 1930663노트

반응식

HRID 1930663 반응식
[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

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 67410437HCID 67410437, 화합물2회

생성물 1

HCID 59333737HCID 59333737, 화합물수율 20.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(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)+;

후처리

  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

출처 및 근거

ORD 기록
ord-d8a13290e7224e6b9fc3cdd412b616f6
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188101B2

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