Sodium hydride → (2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propane-1-sulfonic acid

HRID 1785981Notes

Reaction equation

HRID 1785981 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C@@H:14]([CH3:31])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:35][CH2:36][CH2:37][S:38]([OH:41])(=[O:40])=[O:39]>CN(C=O)C>[C:9]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:35][CH2:36][CH2:37][S:38]([OH:41])(=[O:40])=[O:39])=[CH:27][CH:28]=2)=[O:30])[C@@H:14]([CH3:31])[CH2:13]1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1709623-chloropropane-1-sulfonic AcidHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 11649747(2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-propane-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (207 mg, 0.481 mmol) was dissolved in DMF (5 mL) at room temperature. NaH (58 mg, 2.40 mmol) was added followed by 3-chloro-propane-1-sulfonic acid (sodium salt, 135 mg, 0.60 mmol) and the reaction was allowed to stir over night. The mixture was partitioned between methylene chloride and HCl (1.0N/water), then extracted three times with methylene chloride, dried over MgSO4, filtered and concentrated. The crude residue was purified by preparatory HPLC to afford the product.

Workup

  1. customThe mixture was partitioned between methylene chloride and HCl (1.0N/water)
  2. extractionextracted three times with methylene chloride
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by preparatory HPLC
  7. customto afford the product

Sources & evidence

ORD record
ord-3f3cbef47fbf4db59ebe0ebb6442b3ed
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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