Pyridine-2-carbonyl chloride → HCID 21890473, compound

HRID 721931Notes

Reaction equation

HRID 721931 reaction equation
N1C=CC=CC=1C(Cl)=O.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]2[O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]([N:40]=[C:41]=[S:42])=[O:39]>C1(C)C=CC=CC=1.C(O)C>[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]([N:40]=[C:41]=[S:42])=[O:39].[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]2[O:24][C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:41]([NH:40][C:38]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=2)=[O:39])=[S:42])=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 135034Pyridine-2-carbonyl chlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 21890443HCID 21890443, compound

Product 2

HCID 21890443HCID 21890443, compoundHCID 21890473HCID 21890473, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

2-Pyridinecarbonyl isothiocyanate was prepared using commercially available 2-pyridinecarbonyl 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 2-pyridinecarbonyl 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 (69 mg, yield 90%).

Workup

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

Sources & evidence

ORD record
ord-e052a50fe09b455a9ec8fbd13e8124a0
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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