Guanidinoacetic Acid → {[6-Cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}acetic acid

HRID 2383985노트

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HRID 2383985 반응식
CN(/[CH:4]=[C:5]1\[CH2:6][C:7]([C:14]2[C:22]3[C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[O:19][C:18]=3[C:17]([O:27][CH3:28])=[CH:16][CH:15]=2)([C:12]#[N:13])[CH2:8][CH2:9][C:10]\1=O)C.[CH2:29]([N:33]=[C:34]([NH2:36])[NH2:35])[C:30]([OH:32])=[O:31].[OH-].[Na+]>CO>[C:12]([C:7]1([C:14]2[C:22]3[C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[O:19][C:18]=3[C:17]([O:27][CH3:28])=[CH:16][CH:15]=2)[CH2:8][CH2:9][C:10]2[N:36]=[C:34]([NH:33][CH2:29][C:30]([OH:32])=[O:31])[N:35]=[CH:4][C:5]=2[CH2:6]1)#[N:13]

참가 물질

5

반응물 3

HCID 763Guanidinoacetic AcidHCID 14798Sodium HydroxideHCID 24804131(3E)-3-[(Dimethylamino)methylene]-1-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxocyclohexanecarbonitrile

생성물 1

HCID 24804456{[6-Cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-5,6,7,8-tetrahydroquinazolin-2-yl]amino}acetic acid

시약·촉매·용매 1

HCID 887Methanol용매

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온도
65 °C

실험 절차

A mixture of the compound obtained in example 6 (100 mg, 0.267 mmol), guanidine acetic acid and sodium hydroxide (54 mg, 1 mol) in 10 ml of methanol was stirred at 60-70° C. for 8 hrs. Methanol was evaporated under vacuum and the reaction mass was diluted with 10 ml of water. The aqueous layer was washed with ether, acidified with 0.1 N HCl to pH 2 and extracted with ethyl acetate. The organic layer was washed with water followed by brine, and concentrated under vacuum. The crude product was crystallized form hexane to give 60 mg (52.45% yields) of a yellow colored solid.

후처리

  1. customMethanol was evaporated under vacuum
  2. additionthe reaction mass was diluted with 10 ml of water
  3. washThe aqueous layer was washed with ether
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. concentrationconcentrated under vacuum
  7. customThe crude product was crystallized form hexane
  8. customto give
  9. custom60 mg (52.45% yields) of a yellow colored solid

출처 및 근거

ORD 기록
ord-8e19d433f362462281b2bdac4d7c2524
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263648B2

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