Benzenamine, 3-ethynyl- → HCID 16733971, compound

HRID 2423006Notes

Reaction equation

HRID 2423006 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][C:17](=[O:19])[CH3:18])=[C:9]([O:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:20]([C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25])#[CH:21]>>[ClH:1].[C:20]([C:22]1[CH:23]=[C:24]([NH:25][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:16][C:17](=[O:19])[CH3:18])=[C:9]([O:12][C:13](=[O:15])[CH3:14])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH:26]=[CH:27][CH:28]=1)#[CH:21]

Participants

3

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 272813774-Chloroquinazoline-6,7-diyl diacetate

Product 1

HCID 16733971HCID 16733971, compoundYield 79%

Conditions

Temperature
27.5 °C

Procedure

Into a 2.0 Lt four-necked round-bottomed flask, equipped with a mechanical stirrer, reflux condenser and thermometer socket are charged the organic layer from the previous stage (Step 3) containing 4-Chloro-6,7-diacetoxy-quinazoline and 3-ethynylaniline (20 g). The reaction mass was slowly heated to reach reflux condition and maintained and reflux for 14 hours and the reaction was found to be over by HPLC. Then the reaction was cooled to 25-30° C. and filtered the mass washed the cake with chloroform and dried to get 60 g (79% by theory) of N-(3-ethynylphenyl)-6,7-diacetoxy-4-quinazolinamine hydrochloride as yellow solid.

Workup

  1. customInto a 2.0 Lt four-necked round-bottomed flask, equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionthermometer socket are charged the organic layer from the previous stage (Step 3)
  4. temperatureThe reaction mass was slowly heated
  5. temperatureto reach reflux condition
  6. temperaturemaintained
  7. temperaturereflux for 14 hours
  8. filtrationfiltered the mass
  9. washwashed the cake with chloroform
  10. customdried

Sources & evidence

ORD record
ord-a925205702f2470e9ecdfd9ba66ec60f
Source dataset
uspto-grants-2011_06
Patent number
US07960545B2

Reaction notes

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