Triethylamine → HCID 86647600, compound

HRID 1966819Notes

Reaction equation

HRID 1966819 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[CH2:18][C:17]([CH2:21][CH2:22][OH:23])([CH2:19][OH:20])[O:16][N:15]=3)=[CH:12][N:11]=[C:10]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl.C(Cl)(Cl)Cl>[CH3:36][S:37]([O:20][CH2:19][C:17]1([CH2:21][CH2:22][O:23][S:37]([CH3:36])(=[O:39])=[O:38])[O:16][N:15]=[C:14]([C:13]2[C:8]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:9]3[CH:26]=[N:25][N:24]([CH2:27][CH3:28])[C:10]3=[N:11][CH:12]=2)[CH2:18]1)(=[O:39])=[O:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25073835HCID 25073835, compound

Product 1

HCID 86647600HCID 86647600, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-{3-[4-(Cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-5-(hydroxymethyl)-4,5-dihydroisoxazol-5-yl}ethanol (150 mg, 0.00038 mole) (example 11) was taken in a mixture of dichloromethane and chloroform (10 ml: 10 ml). At 0° C., triethylamine (0.153 g, 0.001513 mole) and methane sulphonyl chloride (0.173 g, 0.001513 mole) were added. The reaction mixture was stirred at 0° C. for about 2 h. The mixture was diluted with dichloromethane and washed with sodium bicarbonate solution. The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo.

Workup

  1. washwashed with sodium bicarbonate solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8097379f78444b2a45a0e6b461bf90b
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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