Triethylamine → HCID 178502673, compound

HRID 626193Notes

Reaction equation

HRID 626193 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:33][O:34][NH:35][CH3:36].CCN(CC)CC>C(Cl)Cl.O>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:35]([O:34][CH3:33])[CH3:36])=[O:8])=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 178418479HCID 178418479, compound

Product 1

HCID 178502673HCID 178502673, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-hydroxynicotinic acid (5.0 g, 1.0 eq), EDCI (8.3 g, 1.2 eq) and HOBt (5.8 g, 1.2 eq) in 150 mL CH2Cl2 were added N-methoxymethanamine hydrochloride (4.2 g, 1.2 eq) and Et3N (14.5 g, 4.0 eq) at rt, the mixture was stirred at rt overnight, water was added, and the mixture was extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (3.5 g, 53% yield). 1H NMR (400 MHz, DMSO-d6) δ 11.82 (brs, 1H), 7.87 (d, J=2.8 Hz, 1H), 7.72 (dd, J=9.6 Hz, 2.8 Hz, 1H), 6.32 (d, J=9.6 Hz, 1H), 3.59 (s, 3H), 3.20 (s, 3H).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. customThe extract was dried
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-e341f8738ae245b796062dc4249f3b80
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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