Dimethyl(methylene)ammounium iodide → HCID 24803117, compound

HRID 2094231Notes

Reaction equation

HRID 2094231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]3[N:23]([CH:24]([CH3:26])[CH3:25])[CH:22]=[N:21][N:20]=3)=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28].[CH3:31][N+:32]([CH3:34])=[CH2:33].[I-]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]3[N:23]([CH:24]([CH3:25])[CH3:26])[C:22]([CH2:31][N:32]([CH3:34])[CH3:33])=[N:21][N:20]=3)=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 59216824HCID 59216824, compound

Product 1

HCID 24803117HCID 24803117, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 25 mL scintillation vial was charged with 4-Chloro-N-[5-chloro-2-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide (60 mg, 0.14 mmol), Eschenmoser salt (25 mg, 0.2 mmol) and anhydrous DMF (2 mL). The resultant mixture was heated to 130° C. and stirred for 3 h. After cooling to room temperature, the residue was purified through preparative HPLC (10% to 90% gradient of MeCN-water) and dried (Lyophilizer) to afford the title compound. 1H NMR (400 MHz, CDCl3) 8.35 (d, 1H), 8.16 (d, 1H), 8.02 (d, 1H), 7.88 (dd, 1H), 7.50 (d. 1H), 5.40 (m, 1H), 3.65 (s, 2H), 2.23 (s, 6H), 1.42 (d, 6H). MS (ES) [M+H]+ expected 537.0. found 537.0.

Workup

  1. customthe residue was purified through preparative HPLC (10% to 90% gradient of MeCN-water)
  2. customdried (Lyophilizer)

Sources & evidence

ORD record
ord-188feb6ef95b44e2a349743b81bec364
Source dataset
uspto-grants-2013_05
Patent number
US08445518B2

Reaction notes

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