Methanesulfonyl chloride → Methanesulfonic acid 2-pyridin-2-yl-3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester

HRID 8237Notes

Reaction equation

HRID 8237 reaction equation
C[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=[CH:20][CH:19]=3)=[C:10]3[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[N:11]3[N:12]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(OCC)(=O)C>[N:7]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[C:8]1[C:9]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)=[C:10]2[CH2:15][CH2:14][CH:13]([CH2:16][O:17][S:29]([CH3:28])(=[O:31])=[O:30])[N:11]2[N:12]=1

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 21992504[2-(6-methyl-pyridin-2-yl)-3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-yl]-methanol

Product 1

HCID 86760183Methanesulfonic acid 2-pyridin-2-yl-3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [2-(6-methyl-pyridin-2-yl)-3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-yl]-methanol (30 mg, 0.07 mmol) and 4-dimethylaminopyridine (catalytic) in pyridine (0.2 mL) is cooled to 0° C. and treated with methanesulfonyl chloride (8 mL, 0.105 mmol) and stirred for 30 min. The mixture is stirred at room temperature for 30 min, diluted with ethyl acetate (20 mL), washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to yield the title compound, 30 mg (86%,) as a yellow oil.

Workup

  1. stirringThe mixture is stirred at room temperature for 30 min
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b3d4902b78f465d8d45d8b15e7477f9
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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