Dimethylformamide → HCID 9804543, compound

HRID 393247Notes

Reaction equation

HRID 393247 reaction equation
[NH2:1][C:2]1(OC)[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1.[H-].[Na+].[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:27]=1[N:33]=[C:34]=[S:35].CN([CH:39]=[O:40])C>>[CH3:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([CH3:25])[C:27]=1[NH:33][C:34]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[C:9]([O:40][CH3:39])[CH:10]=2)[N:5]=[CH:4][N:3]=1)=[S:35]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 879762,6-Xylyl isothiocyanateHCID 178494316HCID 178494316, compound

Product 1

HCID 9804543HCID 9804543, compound

Procedure

A solution of 4-amino-4-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (150 mg) in DMF (4.5 ml) was added to sodium hydride (60% dispersion in mineral oil, 0.03 g) and the reaction mixture was stirred at ambient temperature for 20 minutes. 2,6-Dimethylphenyl isothiocyanate (0.162 g) was added and the mixture was stirred at ambient temperature for 20 hours. The action mixture was evaporated and the residual solid was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and a 2M solution of ammonia in methanol as eluent. There was thus obtained the title compound (0.112 g); NMR Spectrum: (CDCl3) 1.44-1.61 (m, 2H), 1.87-2.08 (m, 5H), 2.32 (s, 3H), 2.36 (s, 6H), 2.94 (d, 2H), 4.04 (m, 5H), 7.1 (s, 1H), 7.19 (m, 3H), 7.29 (s, 1H), 8.69 (s, 1H), 8.9 (s, 1H), 13.37 (s, 1H); Mass Spectrum: M+H+ 466.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 20 hours
  2. customThe action mixture was evaporated
  3. customthe residual solid was purified by column chromatography on silica using
  4. temperatureincreasingly polar mixtures of methylene chloride

Sources & evidence

ORD record
ord-e25cd7d6b70f422aa9f84049863ef708
Source dataset
uspto-grants-2004_10
Patent number
US06806274B1

Reaction notes

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