Methanesulfonamide → HCID 58042470, compound

HRID 2048032Notes

Reaction equation

HRID 2048032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:18][C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11].CCN=C=NCCCN(C)C.Cl.[CH3:40][S:41]([NH2:44])(=[O:43])=[O:42]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([NH:44][S:41]([CH3:40])(=[O:43])=[O:42])=[O:24])=[CH:21][CH:20]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([C:10]([F:11])([F:13])[F:12])[C:14]([F:17])([F:16])[F:15]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58042380HCID 58042380, compound

Product 1

HCID 58042470HCID 58042470, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-chloro-6-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)pyridin-3-ylamino)benzoic acid (Preparation 259, 116 mg, 0.27 mmol) in dichloromethane (5 mL) was added 4-dimethylaminopyridine (50 mg, 0.41 mmol) and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (77 mg, 0.41 mmol). The solution was stirred for 25 minutes at room temperature and methanesulfonamide (39 mg, 0.41 mmol) was added. The reaction mixture was stirred for 18 hours at room temperature. The solution was concentrated in vacuo and the material was purified by reverse phase chromatography eluting with acetonitrile:water (from 5:95 to 95:5, 30 minutes gradient followed by 5 minutes isocratic) to afford the title compound as a white solid (98 mg, 74%).

Workup

  1. stirringThe reaction mixture was stirred for 18 hours at room temperature
  2. concentrationThe solution was concentrated in vacuo
  3. customthe material was purified by reverse phase chromatography
  4. washeluting with acetonitrile

Sources & evidence

ORD record
ord-cdc28efcb3b54517aa6f4436c71b027a
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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