Thiophene → HCID 22368222, compound

HRID 1494656Notes

Reaction equation

HRID 1494656 reaction equation
[NH2:1][C:2]([CH:4]1[N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:8][CH2:7][N:6]([CH2:29][C:30]([NH:32][C:33]2[C:38]([Cl:39])=[CH:37][C:36]([N+:40]([O-])=O)=[CH:35][C:34]=2[Cl:43])=[O:31])[CH2:5]1)=[O:3].S1C=CC=C1.[H][H]>CO.[Pt]>[ClH:39].[ClH:39].[ClH:39].[NH2:1][C:2]([CH:4]1[N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:8][CH2:7][N:6]([CH2:29][C:30]([NH:32][C:33]2[C:34]([Cl:43])=[CH:35][C:36]([NH2:40])=[CH:37][C:38]=2[Cl:39])=[O:31])[CH2:5]1)=[O:3]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 14722643HCID 14722643, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22368222HCID 22368222, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 7 parts of 3-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-N-(2,6-dichloro-4-nitrophenyl)-1-piperazineacetamide, 1 part of a solution of thiophene in methanol 4% and 120 parts of methanol was hydrogenated in a Parr apparatus and at 50° C. with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was converted into the hydrochloride salt in 2-propanol and acetonitrile. The salt was filtered off and dried, yielding 5.55 parts (77.7%) of 3-(aminocarbonyl)-N-(4-amino-2,6-dichlorophenyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide trihydrochloride; mp. 190.8° C. (compound 84).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationThe salt was filtered off
  4. customdried

Sources & evidence

ORD record
ord-340fdbcc2c4343a18ddc7eb11813e911
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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