Water → Methanesulfonic acid 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester

HRID 2279126Notes

Reaction equation

HRID 2279126 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][OH:28])[CH:12]=2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>ClCCl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][O:28][S:37]([CH3:36])(=[O:39])=[O:38])[CH:12]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90013757[6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

Product 1

HCID 90014099Methanesulfonic acid 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 120 mg [6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol and 44 mg of triethylamine in 4 ml of dry dichloromethane was cooled to 0° C. and 47 mg of methanesulfonyl chloride were added. The reaction was brought to room temperature, dichloromethane and water were added and the phasese were separated. The aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulphate, filtrated and concentrated. 170 mg (quant.) of the crude product were obtained as a yellow solid, which was used without further purification.

Workup

  1. customwas brought to room temperature
  2. customthe phasese were separated
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cf6f0425730e4963a3b0eb8dddf42f35
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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