Pyridine-4-carbonyl chloride → HCID 21890954, compound

HRID 721930Notes

Reaction equation

HRID 721930 reaction equation
N1C=CC(C(Cl)=O)=CC=1.[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][C:35]([C:38]([N:40]=[C:41]=[S:42])=[O:39])=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.C(O)C>[N:32]1[CH:37]=[CH:36][C:35]([C:38]([N:40]=[C:41]=[S:42])=[O:39])=[CH:34][CH:33]=1.[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:35]2[CH:34]=[CH:33][N:32]=[CH:37][CH:36]=2)=[O:39])=[S:42])=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 417436Pyridine-4-carbonyl chlorideHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 21890343HCID 21890343, compound

Product 2

HCID 21890343HCID 21890343, compoundHCID 21890954HCID 21890954, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

4-Pyridinecarbonyl isothiocyanate was prepared using commercially available 4-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 4-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 (73 mg, yield 94%).

Workup

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

Sources & evidence

ORD record
ord-a17ec80abdb24f8b9e89eb593015295d
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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