Methanesulfonyl chloride → HCID 88415676, compound

HRID 1037568Notes

Reaction equation

HRID 1037568 reaction equation
[CH:1]1([C:4]2[C:12]([CH:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH2:15][OH:16])=[CH:11][C:10]3[C:6](=[C:7]([C:28]([NH:30][CH3:31])=[O:29])[N:8]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:41][S:42]([O:16][CH2:15][CH2:14][CH:13]([C:12]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:5][C:6]2[C:10]([CH:11]=1)=[N:9][N:8]([C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)[C:7]=2[C:28](=[O:29])[NH:30][CH3:31])[S:17]([CH3:20])(=[O:19])=[O:18])(=[O:44])=[O:43]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67775937HCID 67775937, compound

Product 1

HCID 88415676HCID 88415676, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound (viii) (9 mg, 0.02 mmol) in DCM (4 mL) at 0° C. were added DIPEA (30 μL, 0.17 mmol) and methanesulfonyl chloride (6 μL, 0.078 mmol). The reaction was stirred at 0° C. for 1 h, at which time it was diluted with DCM (12 mL) and saturated aqueous sodium bicarbonate (4 mL). The aqueous layer was separated and extracted with DCM (12 mL). The combined organic layers were washed with water (5 mL), dried (MgSO4) and evaporated to dryness. The residue was purified by flash column chromatography eluting with EtOAc/heptane (50-100%) to afford racemic 3-[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)-2H-indazol-6-yl]-3-(methylsulfonyl)propyl methanesulfonate (ix) as a white solid (8 mg, 69%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with DCM (12 mL)
  3. washThe combined organic layers were washed with water (5 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by flash column chromatography
  7. washeluting with EtOAc/heptane (50-100%)

Sources & evidence

ORD record
ord-14a0951fb31f4b47add33ac819ad0a36
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

Loading…