N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine → HCID 11515072, compound

HRID 1668776Notes

Reaction equation

HRID 1668776 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([CH3:20])[N:11]=2)[CH3:9])=[CH:4][CH:3]=1.[O-:21][C:22]#[N:23].[K+]>CO.Cl.O>[CH3:20][C:12]1[N:11]=[C:10]([N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:22]([NH2:23])=[O:21])=[CH:3][CH:4]=2)[CH3:9])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

6

Reactant 2

HCID 11311597N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamineHCID 11378442Potassium cyanate

Product 1

HCID 11515072HCID 11515072, compoundYield 22.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (4-amino-phenyl)-(2-methyl-quinazolin-4-yl)-methylamine (48 mg, 0.18 mmol) in 250 uL of methanol and 750 uL of 1N HCl was added potassium cyanate (50 mg, 0.62 mmol) in 500 uL of water, and the mixture was stirred overnight at room temperature. The precipitated product was collected by filtration under vacuum, washed with 1 mL of cold water and dried to give the title compound (12.3 mg, 0.04 mmol, 22%). 1H NMR (DMSO): 8.75 (s, 1H), 7.60 (m, 2H), 7.45 (m, 2H), 6.99-7.13 (m, 4H), 5.92 (s, 2H), 3.45 (s, 3H), 2.59 (s, 3H).

Workup

  1. filtrationThe precipitated product was collected by filtration under vacuum
  2. washwashed with 1 mL of cold water
  3. customdried

Sources & evidence

ORD record
ord-6b30fc4bffb849f180fc9216b003dce6
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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