(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → US9290457, Example 6

HRID 927014Notes

Reaction equation

HRID 927014 reaction equation
C([N:3]([C:5](=[O:36])[C:6]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:7]=1[CH:14]1[C:19]([C:20](=O)[CH3:21])=[C:18]([CH3:23])[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[C:16](=[O:34])[N:15]1[CH3:35])[NH2:4])=O.[OH-:37].[CH3:38]OC(NS([N+](CC)(CC)CC)(=O)=O)=O>ClCCl>[C:20]([C:19]1[CH:14]([C:7]2[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:6]=2[C:5]2[O:36][CH:38]=[N:4][N:3]=2)[N:15]([CH3:35])[C:16](=[O:34])[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:31])[F:33])[CH:25]=2)[C:18]=1[CH3:23])(=[O:37])[CH3:21]

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxide2×HCID 1186916972-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-benzoic acid formyl hydrazide2×

Product 1

HCID 118691688US9290457, Example 6

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-benzoic acid formyl hydrazide (intermediate 11) (30.0 mg, 0.06 mmol)) is suspended in dichloromethane (1 mL) and (methoxycarbonylsulfamoyl)triethyl-ammonium hydroxide (Burgess reagent)(35.8 mg, 0.15 mmol) is added. The mixture is stirred at room temperature for 3 days. Additional (methoxycarbonylsulfamoyl)triethyl-ammonium hydroxide (Burgess reagent)(35.8 mg, 0.15 mmol) is added and the reaction is continued for 2 h at 40° C. The solvent is removed under reduced pressure and purification is performed by reversed phase HPLC. Yield: 4 mg; ESI mass spectrum [M+H]+=482; Retention time HPLC: 1.02 min (HPLC method Z018_S04).

Workup

  1. waitthe reaction is continued for 2 h at 40° C
  2. customThe solvent is removed under reduced pressure and purification
  3. custom1.02 min (HPLC method Z018_S04)

Sources & evidence

ORD record
ord-bef481afd49645e4ae17fd2b6c9b59fd
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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