Triethylamine → HCID 86707389, compound

HRID 878754Notes

Reaction equation

HRID 878754 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[N:12]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=1)[S:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([O-:22])=O)=[CH:18][CH:17]=1)(=[O:15])=[O:14].[Na+].C(Cl)(=O)C(Cl)=O.Cl.[CH3:45][O:46][NH2:47].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:45][O:46][NH:47][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][C:16]([S:13]([N:12]([C:3]2[N:4]=[CH:5][C:6]3[C:11]([C:2]=2[CH3:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=2)(=[O:14])=[O:15])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chloride2×HCID 521874O-Methylhydroxylamine hydrochlorideHCID 68289387HCID 68289387, compound

Product 1

HCID 86707389HCID 86707389, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of sodium 4-({(4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)-benzyl]amino}sulfonyl)benzoate (107.7 mg, 0.200 mmol) prepared in Example 2 in chloroform (1 mL) was added oxalyl dichloride (21 μL, 0.240 mmol), and the mixture was stirred at room temperature for 2 hours. Then, thereto was added additional oxalyl dichloride (21 μL, 0.24 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. Then, the resulting residue was suspended in chloroform (1 mL), and added dropwise to a suspension of O-methylhydroxylamine hydrochloride (50.1 mg, 0.600 mmol) and triethylamine (139 μL, 1.00 mmol) in chloroform (1 mL), and the mixture was stirred at room temperature for 1 hour. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→0:10) to give N-methoxy-4-({(4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)benzyl]amino}sulfonyl)-benzamide (88.1 mg, 81%) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→0:10)

Sources & evidence

ORD record
ord-8f1d148be7b64f7693737e41c087b690
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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