Methanesulfonyl chloride → N-(3-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl)methanesulfonamide

HRID 912505Notes

Reaction equation

HRID 912505 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[C:21]([C:23]#[N:24])[C:20]3[N:25]=[CH:26][N:27]([CH3:28])[C:19]=3[CH:18]=2)=[CH:13][C:12]=1[C:29]([F:32])([F:31])[F:30].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:23]([C:21]1[C:20]2[N:25]=[CH:26][N:27]([CH3:28])[C:19]=2[CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[C:12]([C:29]([F:32])([F:30])[F:31])[CH:13]=2)[N:22]=1)#[N:24]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 594106696-[4-(3-aminopropoxy)-3-(trifluoromethyl)-phenyl]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 46830040N-(3-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (31 mg) was added to the solution of 6-[4-(3-Aminopropoxy)-3-(trifluoromethyl)-phenyl]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (20 mg) in DCM (1 ml) containing DIPEA (44 uL). The mixture was stirred at rt for 1 hour, then solvent removed under vacuum and residue dissolved in NMP (1 ml) and purified by HPLC to give expected product, N-(3-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)propyl)methanesulfonamide.

Workup

  1. customsolvent removed under vacuum and residue
  2. dissolutiondissolved in NMP (1 ml)
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-795adcc04a594f96a347d26a9fdc159a
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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