Methyl N-(triethylammoniosulfonyl)carbamate → HCID 86729587, compound

HRID 574198Notes

Reaction equation

HRID 574198 reaction equation
[CH2:1]([O:8][C:9]([CH3:40])([C:36]([F:39])([F:38])[F:37])[C:10]([NH:12][NH:13][C:14]([C:16]1[C:21]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:20][C:19]([C:30]([F:33])([F:32])[F:31])=[C:18]([O:34][CH3:35])[N:17]=1)=[O:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]([C:10]1[O:15][C:14]([C:16]2[C:21]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[CH:20][C:19]([C:30]([F:33])([F:31])[F:32])=[C:18]([O:34][CH3:35])[N:17]=2)=[N:13][N:12]=1)([CH3:40])[C:36]([F:37])([F:38])[F:39])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 86729584HCID 86729584, compound

Product 1

HCID 86729587HCID 86729587, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirring suspension of tert-butyl 2-(2-(2-(benzyloxy)-3,3,3-trifluoro-2-methylpropanoyl)hydrazine carbonyl)-6-methoxy-5-(trifluoromethyl)pyridin-3-ylcarbamate (step 1) (1 g, 1.723 mmol) in dry THF (20 ml) was treated with Burgess reagent (3 equiv.) and heated at reflux under N2 for 1 h 45 min. The RM was reduced in vacuo to approximate volume of 5 ml and diluted with EtOAc (150 ml). The mixture was washed with 2M NaOH, 0.5M HCl, water, brine and dried (MgSO4) and concentrated in vacuo. The crude product was triturated with MeOH to afford the title compound. LC-MS Rt=1.59 min [M+H]+ 563.5 Method High pH_v003.

Workup

  1. temperatureheated
  2. temperatureat reflux under N2 for 1 h 45 min
  3. washThe mixture was washed with 2M NaOH, 0.5M HCl, water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was triturated with MeOH

Sources & evidence

ORD record
ord-ed56d72552894a77ab1eebb8bd5ab338
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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