Isoguvacine → 1-Thiazol-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid

HRID 1246730Notes

Reaction equation

HRID 1246730 reaction equation
CN(C)[S:3]([C:6]1[C:7](Cl)=[N:8][CH:9]=CC=1)(=O)=O.[CH2:14]1[C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH2:17][NH:16][CH2:15]1.[Na].C(O)(C(F)(F)F)=O>C1COCC1.O>[S:3]1[CH:6]=[CH:7][N:8]=[C:9]1[N:16]1[CH2:15][CH:14]=[C:19]([C:20]([OH:22])=[O:21])[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 3765IsoguvacineHCID 6422Trifluoroacetic acidHCID 5360545SodiumHCID 122039042-chloro-N,N-dimethyl-3-pyridinesulfonamide

Product 1

HCID 219047311-Thiazol-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-pyridine-3-sulfonic acid dimethylamide (1.18 mmol) and isoguvacine, sodium salt (2.19 mmol) in THF (0.5 mL) and water (2 mL) was stirred at 90° C. for 22 hours, acidified (pH˜1) with TFA, and extracted with CH2Cl2. The organic layer was dried (Na2SO4), concentrated, and purified by flash chromatography (5% MeOH/CH2Cl2) and trituration (Et2O) to provide as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.47 (dd, J=1.7, 4.8 Hz, 1H), 8.22 (dd, J=1.7, 7.8 Hz, 1H), 7.22 (dd, J=4.8, 7.8 Hz, 1H), 7.03 (sept, J=1.7 Hz, 1H), 3.99 (q, J=3.0 Hz, 2H), 3.40 (t, J=5.6 Hz, 2H), 2.73 (s, 6H), 2.56 (m, 2 H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography (5% MeOH/CH2Cl2) and trituration (Et2O)
  5. customto provide as a white solid

Sources & evidence

ORD record
ord-784264fe04d341e99d74b159e26d8696
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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