3-Hydroxypicolinic Acid → HCID 61535497, compound

HRID 1158587Notes

Reaction equation

HRID 1158587 reaction equation
ClC1C=CC([C:8]2[CH:13]=C[C:11]([C:14]([OH:16])=O)=[C:10]([O:17]C)[CH:9]=2)=CC=1.OC1[C:21]([C:26]([OH:28])=[O:27])=[N:22][CH:23]=CC=1.[CH:29](N(C(C)C)CC)(C)[CH3:30].C[N:39](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:29]([O:28][C:26](=[O:27])[CH2:21][N:22]([C:14]([C:11]1[C:10]([OH:17])=[CH:9][CH:8]=[CH:13][N:39]=1)=[O:16])[CH3:23])[CH3:30]

Participants

7

Reactant 5

HCID 134013-Hydroxypicolinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 248911994-(4-Chlorophenyl)-2-methoxybenzoic acid

Product 1

HCID 61535497HCID 61535497, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation of [(3-hydroxy-pyridine-2-carbonyl)methylamino]acetic acid ethyl ester 31): To a solution of 3-hydroxy picolinic acid (0.40 g, 2.88 mmol) in DMF (5 mL) is added diisopropylethylamine (DIPEA) (1.50 ml, 8.63 mmol), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide (EDCI) (0.825 g, 4.31 mmol) and 1-hydroxybenzotriazole (HOBt) (0.039 g, 0.29 mmol). The reaction mixture is stirred for 5 minutes then methylamino-acetic acid ester hydrochloride (0.663 g, 4.31 mmol) is added. The reaction is stirred at room temperature for 32 hours after which the solvent is removed under reduced pressure. The residue is partitioned between EtOAc and 1M HCl and the organic layer separated, dried (MgSO4), filtered and concentrated under reduced pressure. The crude material is purified over silica (EtOAc:hexanes 1:1) to afford 0.10 g (15% yield) of the desired compound as a colourless solid. HPLC-MS: m/z 240 [M+H]+.

Workup

  1. stirringThe reaction is stirred at room temperature for 32 hours after which the solvent
  2. customis removed under reduced pressure
  3. customThe residue is partitioned between EtOAc and 1M HCl
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material is purified over silica (EtOAc:hexanes 1:1)

Sources & evidence

ORD record
ord-19bd92d38aeb430892f7a6ba7bed5c11
Source dataset
uspto-grants-2010_10
Patent number
US07811595B2

Reaction notes

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