4-Methoxybenzenesulfonyl chloride → HCID 46842450, compound

HRID 1846368Notes

Reaction equation

HRID 1846368 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]2[C:19]2[CH:20]=[C:21]3[CH:27]=[CH:26][NH:25][C:22]3=[N:23][CH:24]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]2[C:19]2[CH:20]=[C:21]3[CH:27]=[CH:26][N:25]([S:38]([C:35]4[CH:34]=[CH:33][C:32]([O:31][CH3:30])=[CH:37][CH:36]=4)(=[O:40])=[O:39])[C:22]3=[N:23][CH:24]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chloride2×HCID 14798Sodium Hydroxide2×HCID 86659821HCID 86659821, compound

Product 1

HCID 46842450HCID 46842450, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-chlorophenyl)-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-4(3H)-one (0.156 g, 0.42 mmol) and benzyltriethylammonium chloride (0.003 g, 0.013 mmol) were combined in CH2Cl2 (10 mL). NaOH powder (0.052 g, 1.31 mmol) was added and the mixture was cool to 0° C. 4-methoxy-benzenesulfonyl chloride (0.107 g, 0.52 mmol) was added, and the reaction mixture was stirred for 30 minutes at 0° C., and warmed to room temperature. After 18 hours, additional NaOH powder (0.050 gm 1.30 mmol), benzyltriethylammonium chloride (0.010 g, 0.04 mmol), and 4-methoxy-benzenesulfonyl chloride (0.200 g, 0.97 mmol) were added and the reaction was continued at room temperature for an additional 6 hours. After concentration and purification by silica gel chromatography, eluting with 100% CH2Cl2 to 100% ethyl acetate to 50% methanol/ethyl acetate, the title compound was afforded as a white solid (0.137 g, 60%). 1H-NMR (300 MHz, DMSO-6): δ8.37 (d, 1.7 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 8.07 (d, J=1.7 Hz, 1H), 7.98 (d, J=8.9 Hz, 2H), 7.88-7.93 (m, 2H), 7.76 (d, J=8.0 Hz, 1H), 7.61-7.66 (m, 1H), 7.34-7.45 (m, 4H), 7.11 (d, J=9.0 Hz, 2H), 6.79 (d, J=3.9 Hz, 1H), 3.82 (s, 3H). MS (APCI) m/z: 543 (M+H)+.

Workup

  1. temperaturewarmed to room temperature
  2. waitAfter 18 hours
  3. waitthe reaction was continued at room temperature for an additional 6 hours
  4. concentrationAfter concentration and purification by silica gel chromatography
  5. washeluting with 100% CH2Cl2 to 100% ethyl acetate to 50% methanol/ethyl acetate

Sources & evidence

ORD record
ord-3350c786277b4e2982c71a591de6e878
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…