Methanesulfonyl chloride → HCID 86668680, compound

HRID 341078Notes

Reaction equation

HRID 341078 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:33](=[O:34])[C:12]2=[CH:13][N:14]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[CH:31][CH:30]=[N:29]4)=[CH:24][CH:23]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]2=[N:10]1.C(N(C(C)C)CC)(C)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>ClCCl>[CH3:44][S:45]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:33](=[O:34])[C:12]2=[CH:13][N:14]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[CH:31][CH:30]=[N:29]4)=[CH:24][CH:23]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]2=[N:10]1)(=[O:47])=[O:46]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68153774HCID 68153774, compound

Product 1

HCID 86668680HCID 86668680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-[2-(Hydroxymethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 654, 0.23 g, 0.51 mmol) was suspended in dichloromethane (5 mL), treated with diisopropylethylamine (0.20 mL, 1.1 mmol, 2.2 equiv) and cooled to −78° C. Methanesulfonyl chloride (60 μL, 0.77 mmol, 1.5 equiv) was added and the mixture was stirred at −78° C. for 30 minutes. The dry ice/acetone bath was removed, the mixture was warmed to ambient temperature and stirred for an additional 45 minutes. The mixture was poured into ammonium chloride (20 mL, aqueous saturated) and extracted with dichloromethane (3×50 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the title compound.

Workup

  1. customThe dry ice/acetone bath was removed
  2. temperaturethe mixture was warmed to ambient temperature
  3. stirringstirred for an additional 45 minutes
  4. additionThe mixture was poured into ammonium chloride (20 mL, aqueous saturated)
  5. extractionextracted with dichloromethane (3×50 mL)
  6. dry with materialThe combined organic extracts were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0be6e18f140f4e4bb8411a3e19a363da
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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