Sodium Hydroxide → 6-(3-Ethylureido)-4-(phenylamino)nicotinic acid

HRID 2174235Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[CH:16]=[C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][N:7]=1)[CH3:2].[OH-].[Na+]>CO.O>[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[CH:16]=[C:15]([NH:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of iii (0.90 g, 2.74 mmol) in MeOH (25 mL) was added a solution of NaOH (0.55 g, 13.70 mmol) in H2O (5 mL). The resulting solution was heated at 70° C. for 3-4 h then cooled to RT and the solvent removed in vacuo. Water was added to the residue and this mixture extracted with EtOAc (2×50 mL). The organic layer was discarded, and the aqueous portion was carefully acidified (under ice-cooling) with 6N HCl till pH 5. The resulting precipitate was filtered, washed with ice-cold water and ether. The off-white solid thus obtained was dried under high vacuum to obtain compound iv (0.70 g, 85%). 1H-NMR (400 MHz, DMSO-d6): δ10.60 (br s, 1H), 9.07 (br s, 1H), 8.55 (s, 1H), 8.0 (br s, 1H), 7.13-7.42 (m, 6H), 3.12 (m, 2H), 1.05 (t, J=7.20 Hz, 3H); [M+H]+ m/z=301.21.

Workup

temperaturethen cooled to RT
customthe solvent removed in vacuo
additionWater was added to the residue
extractionthis mixture extracted with EtOAc (2×50 mL)
temperature(under ice-cooling) with 6N HCl till pH 5
filtrationThe resulting precipitate was filtered
washwashed with ice-cold water and ether
customThe off-white solid thus obtained
customwas dried under high vacuum

Sources & evidence

ORD record: ord-7db6c6891da642f181b2e57936dc647a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09060515B2

Reaction notes

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