Dimethylformamide → (2S,4R)-N-(4-Chloro-phenyl)-N-{1-[4-(4-methanesulfonylamino-3,3-dimethyl-4-oxo-butoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

HRID 1786007Notes

Reaction equation

HRID 1786007 reaction equation
[C:1]([N:4]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:31]=[CH:30][C:20]([O:21][CH2:22][CH2:23][C:24]([CH3:29])([CH3:28])[C:25]([OH:27])=O)=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:32])[CH2:6]1)(=[O:3])[CH3:2].CN(C=O)C.[CH3:45][S:46]([NH2:49])(=[O:48])=[O:47]>C(Cl)Cl.C(Cl)(=O)C(Cl)=O>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([N:4]([C@H:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([C:15](=[O:16])[C:17]3[CH:31]=[CH:30][C:20]([O:21][CH2:22][CH2:23][C:24]([CH3:28])([CH3:29])[C:25]([NH:49][S:46]([CH3:45])(=[O:48])=[O:47])=[O:27])=[CH:19][CH:18]=3)[C@@H:7]([CH3:32])[CH2:6]2)[C:1](=[O:3])[CH3:2])=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 72879MethanesulfonamideHCID 100076874-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2,2-dimethylbutanoic acid

Product 1

HCID 57595491(2S,4R)-N-(4-Chloro-phenyl)-N-{1-[4-(4-methanesulfonylamino-3,3-dimethyl-4-oxo-butoxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 65578Oxalyl chlorideSolvent

Procedure

(2S,4R)-4-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-2,2-dimethyl-butyric acid (200 mg, 0.37 mmol) was dissolved in methylene chloride (5 mL) and oxalyl chloride (2 mL). A single drop of DMF was added, and the mixture was stirred at room temperature until gas evolution ceased. All volatiles were removed. The slurry was dissolved in methylene chloride (10 mL) and triethylamine (2 mL). Methanesulfonamide (200 mg, 2.10 mmol) was added and the reaction mixture was stirred for 3 hours. The mixture was partitioned between methylene chloride and water; the organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by preparatory HPLC.

Workup

  1. customAll volatiles were removed
  2. dissolutionThe slurry was dissolved in methylene chloride (10 mL)
  3. stirringthe reaction mixture was stirred for 3 hours
  4. customThe mixture was partitioned between methylene chloride and water
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by preparatory HPLC

Sources & evidence

ORD record
ord-40840153529243fdbf17ca5637a03392
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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