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

HRID 2383985ノート

反応式

HRID 2383985 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8e19d433f362462281b2bdac4d7c2524
出典データセット
uspto-grants-2012_09
特許番号
US08263648B2

反応ノート

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