Diisopropylethylamine → HCID 58133386, compound

HRID 1042311Notes

Reaction equation

HRID 1042311 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[NH2:21].C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[NH:21][C:9](=[O:11])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 58133386HCID 58133386, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-pyridyl-acetic acid hydrochloride (310 mg) and 2-amino-nicotinic acid methyl ester (270 mg) (Example 1.1) in dichloromethane (5 ml) was added diisopropylethylamine (0.32 ml). The reaction mixture was stirred at ambient temperature for 20 minutes. To this solution was added 4-dimethylaminopyridine (43 mg) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (“EDAC”) (410 mg). The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was partitioned between dichloromethane and water. The phases were separated and the organic layer concentrated. The residue was purified by column chromatography on silica gel (eluent: 15% acetone in dichloromethane) to give 2-(2-pyridin-2-yl-acetylamino)-nicotinic acid methyl ester as a yellow solid (86 mg). 1H-NMR (400 MHz, CDCl3): 11.14 (bs, 1H), 8.63-8.64 (m, 1H), 8.58-8.59 (dd, 1H), 8.25-8.27 (dd, 1H), 7.66-7.70 (m, 1H), 7.38 (d, 1H), 7.20-7.23 (m, 1H), 7.05-7.08 (dd, 1H), 4.11 (s, 2H), 3.92 (s, 3H) ppm.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 20 hours
  2. customThe reaction mixture was partitioned between dichloromethane and water
  3. customThe phases were separated
  4. concentrationthe organic layer concentrated
  5. customThe residue was purified by column chromatography on silica gel (eluent: 15% acetone in dichloromethane)

Sources & evidence

ORD record
ord-79473481ad9448548d7e5c4fc8cf29f2
Source dataset
uspto-grants-2013_10
Patent number
US08557840B2

Reaction notes

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