Benzimidazole → HCID 21847819, compound

HRID 618685Notes

Reaction equation

HRID 618685 reaction equation
Cl.F[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]=[C:6]2[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=1.[N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[NH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:21]1([C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][N:7]=[C:6]3[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[CH:22]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 21847809HCID 21847809, compound

Product 1

HCID 21847819HCID 21847819, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-fluoro-4-(3-methylanilino)quinazoline hydrochloride salt (0.347 g), benzimidazole (0.33 g), potassium carbonate (0.78 g) and DMF (7 ml) was stirred and heated at 150° C. for 24 hours. The mixture was evaporated and the residue was suspended in a mixture of methylene chloride and methanol. The suspension was filtered and the filtrate was evaporated to give a solid which was washed with ethyl acetate and purified by column chromatography using a 24:1 mixture of methylene chloride and methanol as eluent. The resultant solid was triturated with methylene chloride, filtered and dried to give 6-(1-benzimidazolyl)-4-(3-methylanilino)quinazoline (0.2 g), m.p. 245-246° C.; NMR Spectrum: (CD3SOCD3) 2.35 (s, 3H), 6.96-6.99 (d, 1H), 7.27-7.33 (t, 1H), 7.35-7.42 (m, 2H), 7.64-7.77 (m, 3H), 7.82-7.86 (m, 1H), 7.99-8.03 (d, 1H), 8.15-8.20 (m, 1H), 8.66 (s, 2H), 8.90 (d, 1H), 9.80 (s, 1H);

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was suspended in a mixture of methylene chloride and methanol
  3. filtrationThe suspension was filtered
  4. customthe filtrate was evaporated
  5. customto give a solid which
  6. washwas washed with ethyl acetate
  7. custompurified by column chromatography
  8. additiona 24:1 mixture of methylene chloride and methanol as eluent
  9. customThe resultant solid was triturated with methylene chloride
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-65265365b07348018f309fc777dd5a7a
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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