4-(Bis(4-fluorophenyl)methylene)piperidine → 3-[5-[4-(Bis(4-fluorophenyl)methylene]piperidin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione

HRID 1762833Notes

Reaction equation

HRID 1762833 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[C:15]([C:16]([O:18]C)=O)=[CH:14][S:13][CH:12]=1)=[O:9].[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[C:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1.NC1C(C(OC)=O)=CSC=1.BrCCCCCN=C=O>C1(C)C=CC=CC=1>[F:40][C:37]1[CH:38]=[CH:39][C:34]([C:27]([C:24]2[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=2)=[C:28]2[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]3[C:16](=[O:18])[C:15]4=[CH:14][S:13][CH:12]=[C:11]4[NH:10][C:8]3=[O:9])[CH2:30][CH2:29]2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 27244364-(Bis(4-fluorophenyl)methylene)piperidineHCID 2777610Methyl 4-aminothiophene-3-carboxylateHCID 144828831-Bromo-5-isocyanatopentaneHCID 15697668N-(5-bromopentyl)-N'-(4-carbomethoxythien-3-yl)urea

Product 1

HCID 145004073-[5-[4-(Bis(4-fluorophenyl)methylene]piperidin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dioneYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by the procedure of Example 10 using N-(5-bromopentyl)-N'-(4-carbomethoxythien-3-yl)urea (9.01 g, 26 mmol) and 4-[bis(4-fluorophenyl)methylene]piperidine (14.76 g, 52 mmol). The urea was prepared by reacting methyl 4-aminothiophene-3-carboxylate with one equivalent of 5-bromopentylisocyanate in toluene at room temperature for four hours to produce the urea as a tan solid (98% yield). This material was recrystallized from CH2Cl2 /ether/hexane to afford the urea as a white solid, mp 92°-93.5° C.

Workup

  1. customThe urea was prepared
  2. customat room temperature
  3. customfor four hours

Sources & evidence

ORD record
ord-153ba9ed4a9e4ca1a62b14c1f75680db
Source dataset
uspto-grants-1989_05
Patent number
US04835157

Reaction notes

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