Triethylamine → HCID 71599775, compound

HRID 2167776Notes

Reaction equation

HRID 2167776 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([NH:30][CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[O:29])=[C:21]2[CH:20]=1.CCN(CC)CC>C(Cl)Cl>[F:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[C@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]1[CH:24]=[CH:23][N:22]2[N:25]=[CH:26][C:27]([C:28]([NH:30][CH:31]3[CH2:36][CH2:35][N:34]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:33][CH2:32]3)=[O:29])=[C:21]2[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 89618564HCID 89618564, compound

Product 1

HCID 71599775HCID 71599775, compoundYield 133.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methane sulfonyl chloride (10 mg, 0.09 mmol) was added to cold (0-5° C.) solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(piperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide (35 mg, 0.08 mmol) and Et3N (10 mg, 0.1 mmol) in DCM (1 mL); stirring was continued at 25-35° C. for 4 h. Reaction mixture was diluted with DCM, washed with water, aqueous NaHCO3 solution followed by brine to afford the crude compound, which was purified by preparative TLC (using Silicagel GF254, 1000 u coated 20×20 cm dimension glass plate and 10% MeOH in CHCl3 as eluent) to afford 53.63 mg of the title compound.

Workup

  1. customReaction mixture
  2. washwashed with water, aqueous NaHCO3 solution
  3. customto afford the crude compound, which
  4. customwas purified by preparative TLC (using Silicagel GF254, 1000 u coated 20×20 cm dimension glass plate and 10% MeOH in CHCl3 as eluent)

Sources & evidence

ORD record
ord-e5ed044946914dc6a5c8cd669261f137
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

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