Methanesulfonyl chloride → HCID 72706382, compound

HRID 926128Notes

Reaction equation

HRID 926128 reaction equation
CS(O[CH:6]([C:11]1[CH:20]=[N:19][C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[C:16](=[O:30])[N:15]3[N:31]=[CH:32][N:33]=[C:14]3[C:13]=2[CH:12]=1)[C:7]([F:10])([F:9])[F:8])(=O)=O.CS(Cl)(=O)=[O:36].COC1C=CC(CN2[C:51]3[N:52]=[CH:53][C:54](C(O)C(F)(F)F)=C[C:50]=3C3=NC=NN3C2=O)=CC=1>C(Cl)Cl>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:17]2[C:18]3[N:19]=[CH:20][C:11]([CH:6]([N:52]4[CH2:51][CH2:50][O:36][CH2:54][CH2:53]4)[C:7]([F:9])([F:10])[F:8])=[CH:12][C:13]=3[C:14]3=[N:33][CH:32]=[N:31][N:15]3[C:16]2=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 86705397HCID 86705397, compoundHCID 118115349HCID 118115349, compound

Product 1

HCID 72706382HCID 72706382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,2,2-Trifluoro-1-(6-(4-methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-9-yl)ethyl methanesulfonate. Methane sulfonyl chloride (49 μl, 0.63 mmol) was added to a stirred solution of 6-(4-methoxybenzyl)-9-(2,2,2-trifluoro-1-hydroxyethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 87, 127 mg, 0.31 mmol) and TEA (131 μl, 0.94 mmol) in DCM (1.3 mL) and the mixture was stirred for 2 hours. It was diluted with DCM (10 mL), washed with aqueous sodium bicarbonate (5 mL), dried (MgSO4) and concentrated under vacuum to afford the title compound as a brown gum, which was used crude without further purification.

Workup

  1. washwashed with aqueous sodium bicarbonate (5 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0fb8b54735ba4beeb9e6bfe300d8efa2
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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