Hydrochloric Acid → 2-(4-(5-(4-Chlorophenylsulfonamido)quinolin-6-yloxy)-3-methoxyphenyl)acetic acid

HRID 2423319Notes

Reaction equation

[NH2:1][C:2]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][C:14]=2[O:25][CH3:26])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.N1C(C)=CC=CC=1C.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1.[OH-].[Na+].Cl>C1COCC1.CCOC(C)=O.O>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([NH:1][C:2]2[C:11]([O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=3[O:25][CH3:26])=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)(=[O:44])=[O:43])=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 24.4 (36 mg, 0.1 mmol) and 2,6-lutidine (0.024 mL, 0.2 mmol) in THF (0.5 mL) was added 4-chlorobenzenesulfonyl chloride (26 mg, 0.12 mmol). The mixture was stirred at 70° C. overnight. After cooling, water (1 mL) and 10N NaOH (0.5 mL) were added. The mixture was stirred at room temperature for 5 h. 3N HCl (1.7 mL) and EtOAc were added to the mixture, and the organic layer was separated, dried with MgSO4 and concentrated. Flash column chromatography of the residue afforded 24. MS ESI (pos.) m/z: 499.1 (M+H). 1H NMR (DMSO-d6) δ 10.2 (bs, 1H), 8.82 (d, 1H); 8.50 (d, 1H); 7.92 (d, 1H); 7.71 (d, 2H); 7.61 (dd, 1H); 7.55 (d, 2H); 7.03 (d, 1H); 6.95 (d, 1H); 6.79 (dd, 1H); 6.38 (d, 1H); 3.73 (s, 3H); 3.58 (s, 2H).

Workup

temperatureAfter cooling
stirringThe mixture was stirred at room temperature for 5 h
customthe organic layer was separated
dry with materialdried with MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-c8f79682a8d845d8906e7780bca8aa60
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960567B2

Reaction notes

Loading…