Sulfanilamide → HCID 67102425, compound

HRID 2079693Notes

Reaction equation

HRID 2079693 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][C:13]3[CH:14]=[N:15][C:16]([F:19])=[CH:17][CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.BrC1N=CC2C(=C(OC3C=NC(F)=CC=3)C=CC=2)N=1.[S:39]([NH2:49])(=[O:48])([C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=1)=[O:40]>CC(O)C>[F:19][C:16]1[N:15]=[CH:14][C:13]([O:12][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[N:3]=[C:2]([NH:47][C:44]2[CH:45]=[CH:46][C:41]([S:39]([NH2:49])(=[O:40])=[O:48])=[CH:42][CH:43]=2)[N:11]=[CH:10]3)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5333SulfanilamideHCID 866393272-Chloro-8-[(6-fluoro-3-pyridinyl)oxy]quinazolineHCID 86639328HCID 86639328, compound

Product 1

HCID 67102425HCID 67102425, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 0.13 M solution of the 2-chloro-8-(6-fluoropyridin-3-yloxy)quinazoline and 2-bromo-8-(6-fluoropyridin-3-yloxy)quinazoline mixture in i-PrOH was added sulfanilamide (1.0 eq.) and the solution was heated to refluxed for 12 hr. Cooled to room temperature and the precipitate was filtered off and washed with i-PrOH to give the desired product in 61% yield. The solid was 96% pure by HPLC. ES/MS m/z 412.0 (MH+) for 595644-4-(8-(6-fluoropyridin-3-yloxy)quinazolin-2-ylamino)benzenesulfonamide.

Workup

  1. temperaturethe solution was heated
  2. temperatureto refluxed for 12 hr
  3. filtrationthe precipitate was filtered off
  4. washwashed with i-PrOH

Sources & evidence

ORD record
ord-bec4fec69f844529a7a45dd020012dc5
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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