Pyridinium chloride → HCID 131719655, compound

HRID 1900899Notes

Reaction equation

HRID 1900899 reaction equation
C(O)(=O)C.[C:5]([C:8]1[CH:34]=[CH:33][C:11]([C:12]([NH:14][C:15](=[O:32])[NH:16][C:17]2[CH:30]=[CH:29][C:20]([O:21][CH2:22][C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])=[CH:19][C:18]=2[CH3:31])=[O:13])=[CH:10][CH:9]=1)(=[NH:7])[NH2:6].[ClH:35].N1C=CC=CC=1>CO.C(O)(C)C>[ClH:35].[C:5]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15](=[O:32])[NH:16][C:17]2[CH:30]=[CH:29][C:20]([O:21][CH2:22][C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])=[CH:19][C:18]=2[CH3:31])=[O:13])=[CH:33][CH:34]=1)(=[NH:6])[NH2:7]

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 131719654HCID 131719654, compound

Product 1

HCID 131719655HCID 131719655, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3776IsopropanolSolvent

Procedure

A mixture of isopropyl 4-[3-(4-amidinobenzoyl)ureido]-3-methylphenoxyacetate, acetate salt (5 g), and methanol (250 ml) was heated to reflux before a solution of pyridine hydrochloride (1.34 g) in methanol (50 ml) was added. The resultant mixture was heated to reflux until all the solids had dissolved. The hot solution was diluted with isopropanol (100 ml), quickly filtered, and the filtrate was again diluted with isopropanol (100 ml). On storage overnight at 10° C., a solid precipitated which was collected, washed with isopropanol/ether, 1:1, and ether, and dried to give the title compound (4.17 g) as an off-white solid: m.p. 257°-258° C.; NMR Spectrum (DMSO-d6) 1.23 (3H, s), 2.27 (3H, s), 4.70 (2H, s), 5.00 (1H, m), 6.79 (1H, dd), 6.87 (1H, d), 7.75 (1H, d), 7.95 (2H, d), 8.21 (2H, d), 9.30 (2H, br s), 9.54 (2H, br s), 10.48 (1H, s), 11.29 (1H, s); Mass Spectrum m/Z 413 (M+H)+ ; Elemental Analysis: calculated for C21H24N4O5. 1.0 HCl. 0.02 H2O: C, 56.1%; H, 5.62%, N, 12.5%; found: C, 55.8%; H, 5.5%; 12.3%.

Workup

  1. temperaturewas heated
  2. additionwas added
  3. temperatureto reflux until all the solids
  4. dissolutionhad dissolved
  5. filtrationquickly filtered
  6. additionthe filtrate was again diluted with isopropanol (100 ml)
  7. customOn storage overnight at 10° C., a solid precipitated which
  8. customwas collected
  9. washwashed with isopropanol/ether, 1:1, and ether
  10. customdried

Sources & evidence

ORD record
ord-ed3bf966508647f292b124bf071e8da7
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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