Water → HCID 67492882, compound

HRID 43283Notes

Reaction equation

HRID 43283 reaction equation
[C:1](=[O:17])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:18][C:19](=[NH:49])[C:20]1[CH:48]=[CH:47][C:23]([O:24][CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][CH2:36][O:37][C:38]3[CH:46]=[CH:45][C:41]([C:42]([NH2:44])=[NH:43])=[CH:40][CH:39]=3)[CH2:30][CH2:29]2)=[CH:22][CH:21]=1.C(Cl)(Cl)Cl.[OH2:54]>CN(C)C=O>[NH2:49][C:19](=[N:18][C:1]([O:2][CH2:3][CH:4]([CH3:5])[CH3:6])=[O:17])[C:20]1[CH:48]=[CH:47][C:23]([O:24][CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][CH2:36][O:37][C:38]3[CH:39]=[CH:40][C:41]([C:42]([NH2:44])=[N:43][C:1]([O:2][CH2:3][CH:4]([CH3:6])[CH3:5])=[O:54])=[CH:45][CH:46]=3)[CH2:30][CH2:29]2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 6429250Carbonic acid isobutyl ester 4-nitrophenyl esterHCID 9803135T-2307 free base

Product 1

HCID 67492882HCID 67492882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of 1.82 g of isobutyl 4-nitrophenyl 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 left reacting at the same temperature for 17 hours. Chloroform and water were added to the reaction mixture. The organic layer was separated, washed with water, a 5% potassium carbonate aqueous solution and 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 residue 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, 1.43 g of 4-{3-[4-(3-{4-[amino(isobutoxycarbonylimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N′-(isobutoxycarbonyl)benzamidine was obtained as a white solid.

Workup

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

Sources & evidence

ORD record
ord-7655ffef7e074a918409078dba4fa1aa
Source dataset
uspto-grants-2013_09
Patent number
US08536343B2

Reaction notes

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