(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → US9290457, Example 8

HRID 927016Notes

Reaction equation

HRID 927016 reaction equation
C([N:4]([C:6](=[O:37])[C:7]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:8]=1[CH:15]1[C:20]([C:21](=O)[CH3:22])=[C:19]([CH3:24])[N:18]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:17](=[O:35])[N:16]1[CH3:36])[NH2:5])(=O)C.[OH-:38].COC(NS([N+](CC)(CC)[CH2:48][CH3:49])(=O)=O)=O>ClCCl>[C:21]([C:20]1[CH:15]([C:8]2[CH:9]=[CH:10][C:11]([C:13]#[N:14])=[CH:12][C:7]=2[C:6]2[O:37][C:48]([CH3:49])=[N:5][N:4]=2)[N:16]([CH3:36])[C:17](=[O:35])[N:18]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:34])[F:32])[CH:26]=2)[C:19]=1[CH3:24])(=[O:38])[CH3:22]

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 1186916732-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-benzoic acid acetyl hydrazide2×

Product 1

HCID 118691694US9290457, Example 8

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 acetyl hydrazide (intermediate 13) (15 mg, 0.03 mmol) is suspended in dichloromethane (1 mL) and (methoxycarbonylsulfamoyl)triethyl-ammonium hydroxide (Burgess reagent)(17.4 mg, 0.07 mmol) is added. The mixture is stirred at room temperature for 3 days. The solvent is removed under reduced pressure and purification is performed by reversed phase HPLC. Yield: 6.4 mg; ESI mass spectrum [M+H]+=496; Retention time HPLC: 1.04 min (HPLC method Z018_S04).

Workup

  1. customThe solvent is removed under reduced pressure and purification
  2. custom1.04 min (HPLC method Z018_S04)

Sources & evidence

ORD record
ord-7654b0ec4a364ab8ad060ed56a5b15cb
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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