Methyl 4-aminothiophene-3-carboxylate → 3-[4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-butyl]thieno[3,4-d]pyrimidine-2,4-dione

HRID 1762832Notes

Reaction equation

HRID 1762832 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[C:14]([C:15]([O:17]C)=O)=[CH:13][S:12][CH:11]=1)=[O:8].Cl.[F:20][C:21]1[CH:34]=[CH:33][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:22]=1.NC1C(C(OC)=O)=CSC=1.BrCCCCN=C=O>C1(C)C=CC=CC=1>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:15](=[O:17])[C:14]4=[CH:13][S:12][CH:11]=[C:10]4[NH:9][C:7]3=[O:8])[CH2:29][CH2:28]2)=[O:26])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 2777610Methyl 4-aminothiophene-3-carboxylateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 149715841-Bromo-4-isocyanatobutaneHCID 15697666N-(4-bromobutyl)-N'-(4-carbomethoxythien-3-yl)urea

Product 1

HCID 145004063-[4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-butyl]thieno[3,4-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by the procedure of Example 10 using N-(4-bromobutyl)-N'-(4-carbomethoxythien-3-yl)urea (6.92 g, 21 mmol) and 4-(4-fluorobenzoyl)piperidine hydrochloride (10.16 g, 42 mmol). The urea was prepared by reacting methyl 4-aminothiophene-3-carboxylate with 4-bromobutylisocyanate in toluene at room temperature for 12 hours to produce the urea as a tan solid, mp 85°-86° C. There was obtained 3.62 g (40.8% yield) of the title compound as a brown solid. This material was recrystallized from CH2Cl2 /ether, mp 190°-192° C.

Workup

  1. customThe urea was prepared
  2. customat room temperature
  3. customfor 12 hours

Sources & evidence

ORD record
ord-053e608995d74c0e83e1e736e7d465e4
Source dataset
uspto-grants-1989_05
Patent number
US04835157

Reaction notes

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