Hydrochloric Acid → HCID 9825159, compound

HRID 1766601Notes

Reaction equation

HRID 1766601 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=1[CH2:6][O:7][C:8]1[CH:17]=[C:16]([C:18](=[O:30])[NH:19][C:20]2[S:21][C:22]([C:25]([O:27]CC)=[O:26])=[CH:23][N:24]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:31])[CH:14]=2)[N:9]=1.Cl>C1COCC1.O>[Cl:3][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=1[CH2:6][O:7][C:8]1[CH:17]=[C:16]([C:18](=[O:30])[NH:19][C:20]2[S:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][N:24]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:31])[CH:14]=2)[N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21111660HCID 21111660, compound

Product 1

HCID 9825159HCID 9825159, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide solution (0.3 ml of 2M, 0.6 mmol) was added to a stirred suspension of 2-(2-chlorobenzyloxy)-4-[N-(5-ethoxycarbonylthiazol-2-yl)carbamoyl]-6-methylquinoline (Method 1; 0.097 g, 0.202 mmol) in THF (5 ml) and water (2 ml), and the reaction mixture stirred at ambient temperature for 4 hrs. The reaction mixture was adjusted to pH 4–5 with aqueous hydrochloric acid (1M), and concentrated in vacuo. The solid thus precipitated was filtered, washed with water and dried to give the title compound as a colourless solid (0.030 g, 33%). NMR: 2.45 (3H, s), 5.60 (2H, s), 7.40 (3H, m), 7.50 (1H, m), 7.60 (1H, d), 7.65 (1H, m), 7.80 (2H, t), 7.90 (1H, d), 8.15 (1H, s); m/z

Workup

  1. concentrationconcentrated in vacuo
  2. customThe solid thus precipitated
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2d36943dfed744cdb9f5d69bf0e2c2f9
Source dataset
uspto-grants-2007_06
Patent number
US07230108B2

Reaction notes

Loading…