Triethylamine → HCID 178490663, compound

HRID 538785Notes

Reaction equation

HRID 538785 reaction equation
[NH:1]1[CH2:4][CH:3]([CH2:5][N:6]2[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[S:8]/[C:7]/2=[N:15]\[C:16](=[O:26])[C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])[CH2:2]1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C1COCC1.CCOC(C)=O>[C:11]([C:9]1[S:8]/[C:7](=[N:15]\[C:16](=[O:26])[C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])/[N:6]([CH2:5][CH:3]2[CH2:4][N:1]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:2]2)[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178490661HCID 178490661, compound

Product 1

HCID 178490663HCID 178490663, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The TFA salt of Example 63C (0.25 g, 0.64 mmol) was dissolved in 3 mL of THF. The mixture was cooled to 0° C. and triethylamine (0.27 mL, 1.9 mmol) was added. Methanesulfonyl chloride (0.1 ml, 1.3 mMol) was added dropwise and the reaction was stirred at 0° C. for 30 minutes. The reaction was diluted with EtOAc, washed with water, brine, dried with MgSO4 and the solvent removed. Final product was purified by flash chromatography using a gradient from 0 to 100% EtOAc in hexane over 300 mL. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.35 (s, 9H) 2.85 (s, 3H) 3.16-3.30 (m, 1H) 3.84 (dd, J=8.14, 5.76 Hz, 2H) 3.90 (s, 3H) 4.04 (t, J=8.31 Hz, 2H) 4.42 (d, J=7.46 Hz, 2H) 6.63 (s, 1H) 6.92 (d, J=9.16 Hz, 1H) 7.34 (dd, J=8.82, 2.71 Hz, 1H) 7.91 (d, J=2.71 Hz, 1H). MS (DCI/NH3) m/z 472.1 (M+H)+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried with MgSO4
  3. customthe solvent removed
  4. customFinal product was purified by flash chromatography

Sources & evidence

ORD record
ord-444234d6296a4356a0b7e85785f127ef
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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