Hydrochloric Acid → HCID 23370053, compound

HRID 1900900Notes

Reaction equation

HRID 1900900 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]C(C)C)=[O:24])=[CH:19][C:18]=2[CH3:31])=[O:13])=[CH:10][CH:9]=1)(=[NH:7])[NH2:6].O.Cl>C(O)(=O)C>[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]([OH:25])=[O:24])=[CH:19][C:18]=2[CH3:31])=[O:13])=[CH:33][CH:34]=1)(=[NH:6])[NH2:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 131719654HCID 131719654, compound

Product 1

HCID 23370053HCID 23370053, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of isopropyl 4-[3-(4-amidinobenzoyl)ureido]-3-methylphenoxyacetate, acetate salt (500 mg), water (50 ml), 50% aqueous acetic acid (1.5 ml) and 2N HCl (1.5 ml) was stirred and heated to 90°-100° C. until all the solids had dissolved. The hot solution was then quickly filtered and the filtrate was heated to 80°-85° C. and stored at that temperature for 3 days. The mixture was cooled and the solid was collected, washed thoroughly with water, methanol and with ether. The solid was suspended in refluxing methanol/dichloromethane, 4:1 (50 ml). The insoluble material was collected, washed with hot methanol and with ether and dried to give the title compound (250 mg), as a pale yellow solid: NMR Spectrum (DMSO-d6 +CF3CO2H) 2.30 (3H, s), 4.66 (2H, s), 6.81 (1H, dd), 6.89 (1H, d), 7.78 (1H, d), 7.97 (2H, d), 8.24 (2H, d), 9.17 (2H, br s), 9.48 (2H, br s), 10.51 (1H, s), 11.25 (1H, s); m/Z 371 (M+H)+ ; Elemental Analysis: calculated for C18H18N4O5. 1.25 H2O: C, 55.0%; H, 5.26%; N, 14.3%; found: C, 54.9%; H, 5.3%; N, 14.2%.

Workup

  1. temperatureheated to 90°-100° C. until all the solids
  2. dissolutionhad dissolved
  3. filtrationThe hot solution was then quickly filtered
  4. temperaturethe filtrate was heated to 80°-85° C.
  5. temperatureThe mixture was cooled
  6. customthe solid was collected
  7. washwashed thoroughly with water, methanol and with ether
  8. temperaturein refluxing methanol/dichloromethane, 4:1 (50 ml)
  9. customThe insoluble material was collected
  10. washwashed with hot methanol and with ether
  11. customdried

Sources & evidence

ORD record
ord-7dc883ddd3a54a1f86ec7b449d2e6a6b
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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