3-Cyclopentylpropionyl chloride → HCID 21890938, compound

HRID 721906Notes

Reaction equation

HRID 721906 reaction equation
C1(CCC(Cl)=O)CCCC1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][N:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.[CH:33]1([CH2:38][CH2:39][C:40]([N:42]=[C:43]=[S:44])=[O:41])[CH2:37][CH2:36][CH2:35][CH2:34]1>C1(C)C=CC=CC=1.C(O)C>[CH:33]1([CH2:38][CH2:39][C:40]([N:42]=[C:43]=[S:44])=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37]1.[CH:33]1([CH2:38][CH2:39][C:40]([NH:42][C:43]([NH:30][C:29]2[CH:31]=[CH:32][C:26]([O:25][C:16]3[C:15]4[C:20](=[CH:21][C:22]([O:23][CH3:24])=[C:13]([O:12][CH3:11])[CH:14]=4)[N:19]=[CH:18][N:17]=3)=[CH:27][CH:28]=2)=[S:44])=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

7

Reactant 3

HCID 660393-Cyclopentylpropionyl chlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 16775438HCID 16775438, compound

Product 2

HCID 16775438HCID 16775438, compoundHCID 21890938HCID 21890938, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

3-Cyclopentylpropanoyl isothiocyanate was prepared using commercially available 3-cyclopentylpropanoyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 3-cyclopentylpropanoyl isothiocyanate in ethanol (1 ml) was then added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (37 mg, yield 46%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1256a3dd30604d11891b9c852f6c084a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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