Triethylamine → 2-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid

HRID 1984706

Reaction equation

HRID 1984706 reaction equation
C(N(CC)CC)C.Br[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:11]=1.[SH:24][C:25]1[N:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28].C(OCC)(=O)C>CN(C)C=O>[C:20]([O:19][C:17]([NH:16][C:12]1[CH:11]=[C:10]([CH2:9][S:24][C:25]2[C:26]([C:27]([OH:29])=[O:28])=[CH:30][CH:31]=[CH:32][N:33]=2)[CH:15]=[CH:14][N:13]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 220977361,1-Dimethylethyl N-[4-(bromomethyl)-2-pyridinyl]carbamateHCID 178524460HCID 178524460, compound

Product 1

HCID 231509762-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of triethylamine (0.75 mL, 5.4 mmol) in N,N-dimethylformamide (2.0 mL) was added to a solution of 4-bromomethyl-2-tert-butoxycarbonylaminopyridine (Reference compound No. 8-1, 500 mg, 1.7 mmol) and 2-mercaptonicotinic acid (270 mg, 1.7 mmol) in N,N-dimethylformamide (3.0 mL) under ice-cooling, and the mixture was stirred for 12 hours at room temperature. Ethyl acetate (20 mL) was added to the reaction mixture, and the whole was extracted with 0.1N aqueous sodium hydroxide solution (50 mL). 1N Hydrochloric acid was added to the aqueous layer to adjust to pH 5, and the precipitated crystal was filtered off. The crystal was dried under reduced pressure at 60° C. to give 560 mg of the title reference compound as a colorless crystal. (Yield 88%)

Workup

  1. extractionthe whole was extracted with 0.1N aqueous sodium hydroxide solution (50 mL)
  2. addition1N Hydrochloric acid was added to the aqueous layer
  3. filtrationthe precipitated crystal was filtered off
  4. customThe crystal was dried under reduced pressure at 60° C.
  5. customto give 560 mg of the title reference compound as a colorless crystal

Sources & evidence

ORD record
ord-27456374c0c8432d940c7742997ad096
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Linked notes

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