p-Toluenesulfonic acid monohydrate → HCID 67077247, compound

HRID 1959555Notes

Reaction equation

HRID 1959555 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:13][O:14][C:15](=[O:31])[C:16]1[C:21]([CH2:22][O:23]C2CCCCO2)=[C:20]([Cl:30])[CH:19]=[N:18][CH:17]=1>CO>[CH3:13][O:14][C:15](=[O:31])[C:16]1[C:21]([CH2:22][OH:23])=[C:20]([Cl:30])[CH:19]=[N:18][CH:17]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67077953HCID 67077953, compound

Product 1

HCID 67077247HCID 67077247, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Toluenesulfonic acid monohydrate (26.7 mg, 0.140 mmol) was added to a stirred solution of 5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-nicotinic acid methyl ester (20 mg, 0.070 mmol) in MeOH (4 mL). After stirring for 60 min at room temperature, the reaction mixture was concentrated in vacuo and the residue was partitioned between EA (10 mL) and saturated NaHCO3 solution (10 mL). After extraction of the aqueous layer with DCM (2×10 mL) the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 202.0 [M+H+].

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EA (10 mL) and saturated NaHCO3 solution (10 mL)
  3. extractionAfter extraction of the aqueous layer with DCM (2×10 mL) the combined organic layers
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-e830a4c8432b41aca01448ec541da4ba
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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