4-Chloro-6-iodoquinazoline → (1-Benzenesulfonyl-1H-indol-5-yl)-(6-iodo-quinazolin-4-yl)-amine

HRID 983882Notes

Reaction equation

HRID 983882 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2Cl.[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH:18]=[CH:17]2>ClCCCl.C(O)(C)(C)C>[C:26]1([S:23]([N:19]2[C:20]3[C:16](=[CH:15][C:14]([NH:13][C:5]4[C:4]5[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=5)[N:8]=[CH:7][N:6]=4)=[CH:22][CH:21]=3)[CH:17]=[CH:18]2)(=[O:24])=[O:25])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 111738094-Chloro-6-iodoquinazolineHCID 154501451-(Benzenesulfonyl)-1H-indol-5-amine

Product 1

HCID 15450144(1-Benzenesulfonyl-1H-indol-5-yl)-(6-iodo-quinazolin-4-yl)-amineYield 75%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6386tert-ButanolSolvent

Procedure

6-iodo-4-chloroquinazoline 13 (2.38 g, 8.20 mmol) and 5-amino-1-benzenesulfonylindole 21 (2.46 g, 9.00 mmol) were combined in DCE (20 mL) and t-butanol (20 mL). The resulting mixture was heated at reflux under nitrogen for 18 hours to form a bright yellow suspension. Upon cooling the solids were filtered and rinsed with CH2Cl2 and placed under high vacuum to remove any excess solvent. The title compound (3.23 g, 75%) was obtained as a yellow solid. For compound 20: 1H NMR (DMSO-d6; 400 MHz): δ: 10.05 (s, 2H,), 8.93 (s, 1H), 8.53 (s, 1H), 8.25 (m, 1H,), 8.10 (m, 5H), 7.97 (m, 3H), 7.82 (m, 2H), 7.70 (m, 2H), 7.65 (m, 2H), 6.88 (d, 1H, J=3.57 Hz).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under nitrogen for 18 hours
  3. customto form a bright yellow suspension
  4. temperatureUpon cooling the solids
  5. filtrationwere filtered
  6. washrinsed with CH2Cl2
  7. customto remove any excess solvent

Sources & evidence

ORD record
ord-0a2cbb884ecf41c39d408a35b17f52aa
Source dataset
uspto-grants-2005_03
Patent number
US06867201B2

Reaction notes

Loading…