Methyl N-(triethylammoniosulfonyl)carbamate → HCID 71735907, compound

HRID 1615927Notes

Reaction equation

HRID 1615927 reaction equation
[CH:1]1([CH2:4][C:5]([NH:7][NH:8][C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[C:13]([NH:19][CH2:20][C@H:21]3[CH2:23][C@@H:22]3[C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH:12]=[CH:11][N:10]=2)=O)[CH2:3][CH2:2]1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CCOC(C)=O>[CH:1]1([CH2:4][C:5]2[N:10]3[CH:11]=[CH:12][C:13]([NH:19][CH2:20][C@H:21]4[CH2:23][C@@H:22]4[C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]3=[N:8][N:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 86696526HCID 86696526, compound

Product 1

HCID 71735907HCID 71735907, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-cyclopropyl-N′-(4-((((1S,2S)-2-(4-fluorophenyl)cyclopropyl)methyl)amino)-3-(trifluoromethyl)pyridin-2-yl)acetohydrazide (0.06 g, 0.142 mmol) in THF (4 mL) was added Burgess reagent (0.068 g, 0.284 mmol) and the resulting mixture was refluxed stirring for 6 hours. The reaction mixture diluted with EtOAc and extracted with aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with aqueous sodium bicarbonate (2×10 mL) and brine (10 mL), dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography to give 3-(cyclopropylmethyl)-N-(((1S,2S)-2-(4-fluorophenyl)cyclopropyl)methyl)-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-amine as a white solid (0.045 g, 74% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.98 (d, J=7.5 Hz, 1H), 7.09-7.01 (m, 2H), 7.00-6.92 (m, 2H), 6.64 (d, J=7.8 Hz, 1H), 5.49 (d, J=4.0 Hz, 1H), 3.39 (tdd, J=19.0, 12.8, 5.6 Hz, 2H), 3.01 (d, J=6.8 Hz, 2H), 1.92 (dt, J=9.1, 4.9 Hz, 1H), 1.46-1.34 (m, 1H), 1.19-0.94 (m, 3H), 0.65-0.54 (m, 2H), 0.37-0.27 (m, 2H). LCMS M+1=405.05.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. extractionextracted with aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  4. washThe combined organic layers were washed with aqueous sodium bicarbonate (2×10 mL) and brine (10 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dca596a34e394098a666b7337434ac7d
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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