HCID 178486722, compound → HCID 178486726, compound

HRID 890972Notes

Reaction equation

HRID 890972 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]([NH:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])=[N:21][C:22]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:29])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:37][CH3:38])C1C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:36][N:34]([CH3:35])[CH2:33][CH2:32][CH2:31][NH:30][C:20]([NH:21][C:22]1[C:23]([CH3:29])=[CH:24][CH:25]=[CH:26][C:27]=1[CH3:28])=[N:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:37][CH3:38])[CH:11]=2)[N:16]=[CH:15][N:14]=1

Participants

3

Reactant 1

HCID 178486722HCID 178486722, compound

Product 1

HCID 178486726HCID 178486726, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of N-(7-benzyloxy-6-methoxyquinazolin-4-yl)-N′-(3-dimethylaminopropyl)-N″-(2,6-dimethylphenyl)guanidine (2.21 g) and trifluoroacetic acid (40 ml) was stirred and heated to 70° C. for 16 hours. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulphate, filtered and evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and a 2M solution of ammonia gas in methanol as eluent. There was thus obtained the title compound (1.66 g); NMR Spectrum: (DMSOd6, 100° C.) 1.77 (m, 2H), 2.07 (s, 6H), 2.29 (s, 6H), 2.36 (t, 2H), 3.59 (t, 2H), 3.81 (s, 3H), 7.0 (s, 1H), 7.19 (m, 3H), 7.67 (s, 1H), 8.4 (s, 1H), 9.4 (br s, 1H), 10.8 (br s, 1H); Mass Spectrum: M+H+ 423.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue was purified by column chromatography on silica using
  7. temperatureincreasingly polar mixtures of methylene chloride

Sources & evidence

ORD record
ord-7dc13c2dd1074f9497cd6c8e4b2dfd1f
Source dataset
uspto-grants-2006_02
Patent number
US07001904B1

Reaction notes

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