(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 66628316, compound

HRID 2200999Notes

Reaction equation

HRID 2200999 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[N:16][N:17]=[C:13]3[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:11]([CH3:28])=[C:10]2[C:29]([NH2:31])=O)=[CH:5][CH:4]=1)#[N:2].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[N:16][N:17]=[C:13]3[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:11]([CH3:28])=[C:10]2[C:29]#[N:31])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 66628201HCID 66628201, compound

Product 1

HCID 66628316HCID 66628316, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out under argon. (rac)-7-(4-Cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide (10 mg, 24 μmol; prepared analogously to Example 72/73 from Example 70) was initially charged in dry THF (0.6 ml), methoxycarbonylsulfamoyltriethylammonium hydroxide (Burgess reagent; 22 mg, 94 μmol, 4 eq.) was added and the mixture was stirred at RT for 1 h. HPLC showed complete conversion. The reaction mixture was then concentrated and the residue was purified by preparative HPLC (Gromsil C18 column, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). The title compound was obtained as a solid (8.3 mg, 87% of theory).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by preparative HPLC (Gromsil C18 column, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)

Sources & evidence

ORD record
ord-1c7f7bd7c5b64be38a590c8d136bbc67
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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