Methanesulfonamide → HCID 58042372, compound

HRID 2048020Notes

Reaction equation

HRID 2048020 reaction equation
Cl.CN(C)CCCN=C=NCC.[Cl:13][C:14]1[CH:22]=[C:21]([O:23][C:24]2[CH:25]=[N:26][C:27]([CH:31]3[CH2:33][CH2:32]3)=[C:28]([Cl:30])[CH:29]=2)[C:20]([Cl:34])=[CH:19][C:15]=1[C:16](O)=[O:17].[CH3:35][S:36]([NH2:39])(=[O:38])=[O:37]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:13][C:14]1[CH:22]=[C:21]([O:23][C:24]2[CH:25]=[N:26][C:27]([CH:31]3[CH2:33][CH2:32]3)=[C:28]([Cl:30])[CH:29]=2)[C:20]([Cl:34])=[CH:19][C:15]=1[C:16]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])=[O:17]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58042467HCID 58042467, compound

Product 1

HCID 58042372HCID 58042372, compoundYield 12.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Dimethylaminopyridine (51 mg, 0.42 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (80 mg, 0.42 mmol) were added to a suspension of 2,5-dichloro-4-(5-chloro-6-cyclopropylpyridin-3-yloxy)benzoic acid (Preparation 220, 100 mg, 0.28 mmol) in dichloromethane (3 mL). The reaction mixture was stirred at room temperature for 20 minutes. Methylsulfonamide (40 mg, 0.42 mmol) was added and the reaction mixture was stirred at room temperature for 18 hours before concentrating in vacuo. The crude compound was purified by reverse phase column chromatography eluting with acetonitrile:water (from 5:95 to 95:5) followed by preparative HPLC to afford the title compound (15.1 mg, 12%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. concentrationbefore concentrating in vacuo
  3. customThe crude compound was purified by reverse phase column chromatography
  4. washeluting with acetonitrile

Sources & evidence

ORD record
ord-6327d7bcdd494ea7abaa686ffd568ba4
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

Loading…