Triethylamine → HCID 22612202, compound

HRID 844031Notes

Reaction equation

HRID 844031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[N:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:5]=[N:6][CH:7]=1.Cl.[NH2:19][CH2:20][CH:21]1[CH2:23][CH2:22]1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[N:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)=[O:13])[CH:5]=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21883477Ethylcarbodiimide hydrochlorideHCID 22612082HCID 22612082, compound

Product 1

HCID 22612202HCID 22612202, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(5-chloro-pyridin-3-yloxy)-nicotinic acid (0.200 grams, 0.88 mmole), aminomethylcyclopropane hydrochloride (0.094 grams, 0.88 mmole), triethylamine (0.089 grams, 0.88 mmole) and 1-hydroxybenzotriazole hydrate (0.119 grams, 0.88 mmole) in dry dimethylformamide (3 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.164 grams, 0.96 mmole) and stirred over night. The mixture was poured into 100 ml water and extracted with ethyl acetate. The combined organics were washed with 1 N NaOH, water and brine, dried over MgSO4, filtered and concentrated to give an oil that was purified by chromatography on silica gel eluting with 2.5% methanollmethylene chloride. Recrystalization from ethyl acetate/hexane gave a white solid (0.163 g). M.P. 105-107° C.; Anal. calcd. for C15H14N3O2Cl: C, 59.31;H, 4.65; N, 13.83. Found: C, 59.41;H, 4.68; N, 13.44.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with 1 N NaOH, water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas purified by chromatography on silica gel eluting with 2.5% methanollmethylene chloride
  8. customRecrystalization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e00851cd03b14964a4bb3781f187f594
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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