Hydrochloric Acid → HCID 23112227, compound

HRID 2264349Notes

Reaction equation

HRID 2264349 reaction equation
C(Cl)(Cl)[Cl:2].[S:5]1[C:9]2[CH:10]=[CH:11][C:12]([NH:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:19]([CH2:29]Cl)[CH:18]=3)=[O:16])=[CH:13][C:8]=2[N:7]=[CH:6]1.[NH:31]1[CH2:36][CH2:35][CH:34]([C:37]([NH2:39])=[O:38])[CH2:33][CH2:32]1.Cl>C(OCC)(=O)C.C(O)C>[ClH:2].[S:5]1[C:9]2[CH:10]=[CH:11][C:12]([NH:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:19]([CH2:29][N:31]4[CH2:36][CH2:35][CH:34]([C:37]([NH2:39])=[O:38])[CH2:33][CH2:32]4)[CH:18]=3)=[O:16])=[CH:13][C:8]=2[N:7]=[CH:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 37724-PiperidinecarboxamideHCID 6212ChloroformHCID 23112212N-5-Benzothiazolyl-2-(chloromethyl)[1,1′-biphenyl]-4-carboxamide

Product 1

HCID 23112227HCID 23112227, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10 ml of chloroform were added 250 mg of N-1,3-benzothiazol-5-yl-2-(chloromethyl)biphenyl-4-carboxamide and 169 mg of piperidine-4-carboxamide, followed by 3 days of stirring at room temperature. The reaction solvent was removed by evaporation under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform:methanol) to obtain a yellow foamy substance. Thereto were added 2 ml of ethanol and 1 ml of a 4M ethyl acetate solution of hydrochloric acid, followed by removal of the solvent under reduced pressure. The residue was crystallized (ethanol:water:ethyl acetate) to obtain 205 mg of 1-({4-[(1,3-benzothiazol-5-ylamino)carbonyl]biphenyl-2-yl}methyl)piperidine-4-carboxamide hydrochloride.

Workup

  1. customThe reaction solvent was removed by evaporation under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol)
  3. customto obtain a yellow foamy substance
  4. customfollowed by removal of the solvent under reduced pressure
  5. customThe residue was crystallized (ethanol:water:ethyl acetate)

Sources & evidence

ORD record
ord-7672abb310cc4ad6b2ad94b566232a93
Source dataset
uspto-grants-2010_12
Patent number
US07855198B2

Reaction notes

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