Triethylamine → 2-[4-(2-Benzoxazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamine

HRID 1156022Notes

Reaction equation

HRID 1156022 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[C:5]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:4]=1.C(N(CC)CC)C.[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1S>C(O)CCC>[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[N:20]1[CH2:21][CH2:22][N:17]([C:5]2[N:4]=[C:3]([NH2:2])[C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 204738332-Piperazine-4-amino-6,7-dimethoxyquinazoline hydrochlorideHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 130363872-[4-(2-Benzoxazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamineYield 6.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a suspension of 4-amino-6,7-dimethoxy-2-(1-piperazinyl)quinazoline hydrochloride (3.26 g ) in 250 ml of butanol, 1.01 g of triethylamine was added. The mixture was stirred at room temperature for 2 hr and 1.51 g of benzoxazole-2-thiol was added. The mixture was refluxed for 72 hr and evaporated. The solids were triturated with water and filtered to give 2.7 g of crude product. This was chromatographed over silica gel using 7% methanol-methylene chloride as eluent. Appropriate fractions were mixed together to give 0.25 g of the title compound, which was crystallized from hexane-methylene chloride; mp>250° C.; ir (nujol mull) 3420, 3320 and 3200 cm-1 ; uv max (MeOH) 341 (ε=6,650), 282 (ε=28,900), 278 (ε=29,300) and 252 nm (ε=73,000); and Anal. Calcd for C21H22N6O3 : C, 62.06% H, 5.45% N, 20.68% and Found: C, 61.38% H, 5.59% N, 20.78%.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 72 hr
  3. customevaporated
  4. customThe solids were triturated with water
  5. filtrationfiltered
  6. customto give 2.7 g of crude product
  7. customThis was chromatographed over silica gel using 7% methanol-methylene chloride as eluent
  8. additionAppropriate fractions were mixed together

Sources & evidence

ORD record
ord-88ed1fac7eec4374b2da449268a87201
Source dataset
uspto-grants-1982_06
Patent number
US04333937

Reaction notes

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