Methyl N-(triethylammoniosulfonyl)carbamate → HCID 78164246, compound

HRID 1615932Notes

Reaction equation

HRID 1615932 reaction equation
[F:1][C:2]([F:32])([F:31])[CH2:3][C:4]([NH:6][NH:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[C:12]([N:18]([CH2:20][CH:21]2[CH2:23][CH:22]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH3:19])[CH:11]=[CH:10][N:9]=1)=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CCOC(C)=O>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH:22]2[CH2:23][CH:21]2[CH2:20][N:18]([CH3:19])[C:12]2[CH:11]=[CH:10][N:9]3[C:4]([CH2:3][C:2]([F:32])([F:31])[F:1])=[N:6][N:7]=[C:8]3[C:13]=2[C:14]([F:17])([F:16])[F:15])=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 86696532HCID 86696532, compound

Product 1

HCID 78164246HCID 78164246, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3,3,3-trifluoro-N′-(4-(((2-(4-fluorophenyl)cyclopropyl)methyl)(methyl)amino)-3-(trifluoromethyl)pyridin-2-yl)propanehydrazide (0.5 g, 1.077 mmol) and Burgess reagent (0.513 g, 2.153 mmol) in THF (10 mL) was heated to reflux stirring for 90 min. The reaction mixture was diluted with EtOAc and washed with aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were washed with aqueous sodium bicarbonate (2×20 mL), dried with brine (20 mL), dried over magnesium sulfate, and concentrated. The residue was purified by silica gel chromatography using 0-100% EtOAc/hexane as the eluent to give N-((2-(4-fluorophenyl)cyclopropyl)methyl)-N-methyl-3-(2,2,2-trifluoroethyl)-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-amine as a yellow solid (0.14 g, 26.5%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.91 (d, J=7.8 Hz, 1H), 7.03-6.91 (m, 4H), 6.83 (d, J=7.8 Hz, 1H), 4.02 (q, J=9.8 Hz, 2H), 3.48 (dd, J=14.1, 6.0 Hz, 1H), 3.33 (dd, J=14.1, 7.3 Hz, 1H), 3.16 (s, 3H), 1.77 (dd, J=9.0, 4.8 Hz, 1H), 1.34-1.23 (m, 1H), 1.05 (dt, J=8.5, 5.4 Hz, 1H), 0.91 (dt, J=8.8, 5.5 Hz, 1H). LCMS: M+1=447.12.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. washwashed with aqueous sodium bicarbonate
  4. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  5. washThe combined organic layers were washed with aqueous sodium bicarbonate (2×20 mL)
  6. dry with materialdried with brine (20 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5b61031b6c9442358c20602173fe7d05
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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