Triethylamine → HCID 86601189, compound

HRID 1245335Notes

Reaction equation

HRID 1245335 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[O:9][C:10]1[CH:22]=[CH:21][C:13]2[C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][O:16][C:12]=2[C:11]=1[CH2:23][CH2:24][CH3:25].CCN(CC)CC.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[CH3:33][S:34]([O:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[O:9][C:10]1[CH:22]=[CH:21][C:13]2[C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][O:16][C:12]=2[C:11]=1[CH2:23][CH2:24][CH3:25])(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69663791HCID 69663791, compound

Product 1

HCID 86601189HCID 86601189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-{[cis-2-(hydroxymethyl)cyclohexyl]oxy}-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole (388 mg, 1.09 mmol), from this Example step 3, in CH2Cl2 (11 mL) was added Et3N (0.230 ml, 1.635 mmol) at 0° C., followed by methanesulfonyl chloride (0.093 mL, 1.2 mmol). The reaction mixture was stirred from 0° C. to room temperature for four hours. The mixture was diluted with CH2Cl2, washed with 5% HCl, followed by H2O then NaHCO3. Organic extracts were dried over NaSO4 and filtered. The solvent was evaporated in vacuo to give title compound.

Workup

  1. customat 0° C.
  2. washwashed with 5% HCl
  3. dry with materialOrganic extracts were dried over NaSO4
  4. filtrationfiltered
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b13b8c12dc2e4c1a8645dd3fc61857f9
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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