Water → HCID 178490699, compound

HRID 1888681Notes

Reaction equation

HRID 1888681 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([CH:10]([OH:12])[CH3:11])/[C:7](=[N:13]/[C:14](=[O:24])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])/[S:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34].O>C(Cl)Cl>[CH3:32][S:33]([O:12][CH:10]([C:8]1=[CH:9][N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[S:6]/[C:7]/1=[N:13]\[C:14]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])=[O:24])[CH3:11])(=[O:35])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178490698HCID 178490698, compound

Product 1

HCID 178490699HCID 178490699, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the product of Example 163 (220 mg, 0.6 mmol) in CH2Cl2 (20 mL) and triethylamine (181 mg, 1.8 mmol) was cooled to 0° C., and treated dropwise with methanesulfonyl chloride (102 mg, 0.9 mmol). The reaction was stirred at 0° C. for 30 min., poured into water, and the mixture was extracted with CH2Cl2 (2×). The organics were combined, dried over MgSO4, filtered and concentrated to afford the title compound (234 mg, 88%). MS (DCI/NH3) m/z 383 (M−Ms+15)+.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (2×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f5ba6602257b49a29f1730ce346ee3b4
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Reaction notes

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