Triethylamine → HCID 86637298, compound

HRID 1876882Notes

Reaction equation

HRID 1876882 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([C:14]3([CH2:18][C:19]#[N:20])[CH2:17][NH:16][CH2:15]3)[CH:13]=2)[CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[CH2:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>ClCCl>[Cl:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([C:14]3([CH2:18][C:19]#[N:20])[CH2:17][N:16]([S:30]([CH2:28][CH3:29])(=[O:32])=[O:31])[CH2:15]3)[CH:13]=2)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 86637299HCID 86637299, compound

Product 1

HCID 86637298HCID 86637298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-ylacetonitrile hydrochloride (1.42 g, 0.00456 mol) in dichloromethane (30 mL) was added triethylamine (1.59 mL, 0.0114 mol) followed by ethanesulfonyl chloride (0.497 mL, 0.00525 mol) at 0° C. The reaction was stirred at room temperature for 1 h, quenched with 1N HCl. The organic layer was separated, washed with aqueous sodium bicarbonate, dried over sodium sulfate, and evaporated to dryness. The crude product was used directly in next step (1.26 g, 75.3%). LCMS (M+H) 367.3.

Workup

  1. customquenched with 1N HCl
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9bc4fb68df52404faa078bb1097148e5
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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