Water → 4-{3-[4-(3-{4-[amino(propoxycarbonylimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-(propoxycarbonyl)benzamidine

HRID 43281ノート

反応式

HRID 43281 の反応式
[C:1](=[O:16])([O:12][CH2:13][CH2:14][CH3:15])OC1C=CC([N+]([O-])=O)=CC=1.[NH2:17][C:18](=[NH:48])[C:19]1[CH:47]=[CH:46][C:22]([O:23][CH2:24][CH2:25][CH2:26][CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][O:36][C:37]3[CH:45]=[CH:44][C:40]([C:41]([NH2:43])=[NH:42])=[CH:39][CH:38]=3)[CH2:29][CH2:28]2)=[CH:21][CH:20]=1.C(Cl)(Cl)Cl.[OH2:53]>CN(C)C=O>[NH2:48][C:18](=[N:17][C:1]([O:12][CH2:13][CH2:14][CH3:15])=[O:16])[C:19]1[CH:47]=[CH:46][C:22]([O:23][CH2:24][CH2:25][CH2:26][CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][O:36][C:37]3[CH:38]=[CH:39][C:40]([C:41]([NH2:43])=[N:42][C:1]([O:12][CH2:13][CH2:14][CH3:15])=[O:53])=[CH:44][CH:45]=3)[CH2:29][CH2:28]2)=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 962WaterHCID 6212ChloroformHCID 9803135T-2307 free baseHCID 544839324-Nitrophenyl propyl carbonate

生成物 1

HCID 674924024-{3-[4-(3-{4-[amino(propoxycarbonylimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-(propoxycarbonyl)benzamidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Into a solution of 1.71 g of 4-nitrophenyl propyl carbonate in 15 mL of N,N-dimethylformamide, 1.50 g of 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine was added at room temperature, and the solution was stirred at the same temperature for 4 hours. Chloroform and water were added to the reaction mixture. The organic layer was separated, washed with water, twice with a 5% potassium carbonate aqueous solution and with a saturated sodium chloride aqueous solution successively, and dried over anhydrous magnesium sulfate, followed by solvent removal by evaporation under reduced pressure. The obtained residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=4:1). The obtained solid substance was dissolved in chloroform, washed with a 5% potassium carbonate aqueous solution and a saturated sodium chloride aqueous solution successively, and dried over anhydrous magnesium sulfate. After removing the solvent by evaporation under reduced pressure, 1.25 g of 4-{3-[4-(3-{4-[amino(propoxycarbonylimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N′-(propoxycarbonyl)benzamidine was obtained as a white solid.

後処理

  1. customThe organic layer was separated
  2. washwashed with water, twice with a 5% potassium carbonate aqueous solution and with a saturated sodium chloride aqueous solution successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customfollowed by solvent removal by evaporation under reduced pressure
  5. customThe obtained residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=4:1)
  6. dissolutionThe obtained solid substance was dissolved in chloroform
  7. washwashed with a 5% potassium carbonate aqueous solution
  8. dry with materiala saturated sodium chloride aqueous solution successively, and dried over anhydrous magnesium sulfate
  9. customAfter removing the solvent
  10. customby evaporation under reduced pressure

出典と根拠

ORDレコード
ord-9905b1c3996948a3abc0f58bc887e460
出典データセット
uspto-grants-2013_09
特許番号
US08536343B2

反応ノート

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