Triethylamine → HCID 9976683, compound

HRID 233560Notes

Reaction equation

HRID 233560 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:7]=[CH:6]1.CCN(CC)CC.[CH3:30][S:31](Cl)(=[O:33])=[O:32].[OH-].[Na+]>C(Cl)Cl.C(Cl)Cl.CO>[CH3:30][S:31]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)=[C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:7]=[CH:6]1)(=[O:33])=[O:32]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 10424642HCID 10424642, compound

Product 1

HCID 9976683HCID 9976683, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To the compound of Example 4, described above (79 mg, 0.26 mmol) in CH2Cl2 (0.5 mL) was added Et3N (72 uL, 0.52 mmol), and then methanesulfonyl chloride (25 uL, 0.31 mmol). The reaction exothermed to CH2Cl2 reflux briefly. The reaction was over within 1 min based on tlc (19:1 CH2Cl2 /MeOH) and was poured into 10% NaOH (5 mL) and extracted with EtOAc (3×20 mL). The extracts were washed with H2O (10 mL) and said aq Nacl (10 mL), dried (Na2SO4), concentrated and flash chromatographed (1×10 cm silica) with 0-8% MeOH in CH2Cl2 to afford 63 mg (65%). mp=186°-187°.

Workup

  1. temperaturereflux briefly
  2. customwas over within 1 min
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe extracts were washed with H2O (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customflash chromatographed (1×10 cm silica) with 0-8% MeOH in CH2Cl2
  8. customto afford 63 mg (65%)

Sources & evidence

ORD record
ord-4bb323961b7e4310b074dfba8587373f
Source dataset
uspto-grants-1997_01
Patent number
US05593992

Reaction notes

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