Methyl 6-(3,5-dichloro-4-ethoxyphenylcarbamoyl)nicotinate → HCID 67041672, compound

HRID 62727Notes

Reaction equation

HRID 62727 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][N:16]=2)=[O:14])[CH:5]=[C:6]([Cl:11])[C:7]=1[O:8][CH2:9][CH3:10]>CO>[Cl:11][C:6]1[CH:5]=[C:4]([NH:12][C:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]=2)=[O:14])[CH:3]=[C:2]([Cl:1])[C:7]=1[O:8][CH2:9][CH3:10]

Participants

3

Reactant 1

HCID 67041919Methyl 6-(3,5-dichloro-4-ethoxyphenylcarbamoyl)nicotinate

Product 1

HCID 67041672HCID 67041672, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(3,5-Dichloro-4-ethoxyphenylcarbamoyl)nicotinic acid (AAA-020) (19 mg, 109%) was prepared from methyl 6-(3,5-dichloro-4-ethoxyphenylcarbamoyl)nicotinate (3) (18 mg, 49 μmol) using a procedure essentially the same as in Step (iii) for AAA-013, except methanol (0.5 mL) was also added and the reaction mixture was stirred at RT overnight: m/z 353 [M−H]− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 11.12 (1H, s), 9.18 (1H, dd), 8.55 (1H, dd), 8.29 (1H, dd), 8.13 (2H, s), 4.06 (2H, q), 1.37 (3H, t).

Sources & evidence

ORD record
ord-4724338419794035b34bab0262833352
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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