Acetic Acid → HCID 14722638, compound

HRID 1073192Notes

Reaction equation

HRID 1073192 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([NH:9][C:10](=[O:38])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:14][CH:13]2[CH3:37])=[C:4]([Cl:39])[CH:3]=1.C(O)(=O)C.[O-:44][C:45]#[N:46].[K+]>O>[NH2:46][C:45]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([NH:9][C:10](=[O:38])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[CH2:14][CH:13]2[CH3:37])=[C:4]([Cl:39])[CH:3]=1)=[O:44]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 14722630HCID 14722630, compound

Product 1

HCID 14722638HCID 14722638, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4.5 parts of N-(4-amino-2,6-dichlorophenyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-2-methyl-1-piperazineacetamide in 60 parts of acetic acid was added dropwise a solution of 1.02 parts of potassium cyanate in 17 parts of water. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was evaporated and the residue was taken up in water. The whole was treated with an ammonium hydroxide solution and the product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The second fraction was collected and the eluent was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.49 parts (51.9%) of N-[4-[(aminocarbonyl)amino]-2,6-dichlorophenyl]-4-[5,5-bis(4-fluorophenyl)pentyl]-2-methyl-1-piperazineacetamide; mp. 119.9° C. (compound 76).

Workup

  1. customThe reaction mixture was evaporated
  2. additionThe whole was treated with an ammonium hydroxide solution
  3. extractionthe product was extracted twice with dichloromethane
  4. washThe combined extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe second fraction was collected
  11. customthe eluent was evaporated
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-f9d7dd11d00c44f3b45290a1030be6ed
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

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