Triethylamine → HCID 59843169, compound

HRID 2196522Notes

Reaction equation

HRID 2196522 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][N:12]=2)[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH3:30][S:31]([O:18][CH2:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([N:10]2[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][C:8]([C:19]([F:20])([F:21])[F:22])=[N:9]2)[CH:16]=1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59843160HCID 59843160, compound

Product 1

HCID 59843169HCID 59843169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 37 (215 mg, 0.695 mmol) in dichloromethane (6.95 mL) at 0° C. was added triethylamine (0.388 mL, 2.78 mmol) followed by methanesulfonyl chloride (0.163 mL, 2.092 mmol). The resulting solution was allowed to stir at room temperature for 1 h. The solvent was evaporated. The mixture was quenched with a saturated sodium carbonate solution and extracted with ethyl acetate, washed with brine, dried (MgSO4) filtered and concentrated. Compound 38 was isolated as an orange solid and used as is for the next step. LRMS (ESI): calc. 387.1; found 388.1 (MH)+.

Workup

  1. customThe solvent was evaporated
  2. customThe mixture was quenched with a saturated sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0f292548cd9a487f9b331cdf0051f461
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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