Formaldehyde → N-isopropyl-2-(6-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl)acetamide

HRID 77402

반응식

HRID 77402 반응식
[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]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:13]([CH2:25][C:26]([NH:28][CH:29]([CH3:31])[CH3:30])=[O:27])[C:12]2=[O:32].C=O.[C:35]([BH3-])#N>C(#N)C.C(O)(=O)C.CO>[CH:29]([NH:28][C:26](=[O:27])[CH2:25][N:13]1[C:12](=[O:32])[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([N:2]3[CH2:3][CH:4]4[CH:5]([CH2:6][N:7]([CH3:35])[CH2:8]4)[CH2:1]3)[CH:10]=2)[N:15]=[C:14]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:30])[CH3:31]

참가 물질

7

반응물 3

HCID 712FormaldehydeHCID 498716Cyano-borohydrideHCID 699294986-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl-N-isopropylacetamide

생성물 1

HCID 69929834N-isopropyl-2-(6-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl)acetamide수율 39.1%

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 887Methanol용매HCID 6342Acetonitrile용매

반응 조건

온도
130 °C

실험 절차

2-(6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl-N-isopropylacetamide (EXAMPLE 4A) (100 mg, 0.23 mmol) was dissolved in acetonitrile (2 mL) before addition of formaldehyde (28 mg, 0.35 mmol) and MP-cyanoborohydride (140 mg, 0.36 mmol) followed by 2 drops of acetic acid. The resulting solution was sealed in a microwave vial and heated at 130° C. for 20 minutes. Reaction mixture was then diluted with methanol before loading directly onto a 1 g SCX cartridge. The crude material was purified by SCX. The solvent was removed under reduced pressure and then re-dissolved in methanol (1 mL) and purified by preparative-HPLC. Purified sample was free-based using 500 mg SCX cartridge to afford N-isopropyl-2-(6-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-4-oxo-2-phenylquinazolin-3(4H)-yl)acetamide (38 mg, 0.09 mmol).

후처리

  1. customThe resulting solution was sealed in a microwave vial
  2. customReaction mixture
  3. customThe crude material was purified by SCX
  4. customThe solvent was removed under reduced pressure
  5. dissolutionre-dissolved in methanol (1 mL)
  6. custompurified by preparative-HPLC
  7. customPurified sample

출처 및 근거

ORD 기록
ord-c63974b16b5b4b1a92f85b9e477cc612
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841289B2

연결된 노트

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