Sodium Hydroxide → {6-Chloro-3-methyl-4-[4-(3-phenyl-ureido)-phenyl]-naphthalen-2-yl}-acetic acid

HRID 1468464Notes

Reaction equation

HRID 1468464 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:24])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:32])[CH:11]=2)[CH:6]=1.[OH-].[Na+]>C(O)C.C1COCC1>[Cl:32][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[C:14]([CH3:15])=[C:13]2[C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:24])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86695036{6-Chloro-3-methyl-4-[4-(3-phenyl-ureido)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

Product 1

HCID 71711715{6-Chloro-3-methyl-4-[4-(3-phenyl-ureido)-phenyl]-naphthalen-2-yl}-acetic acidYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {6-chloro-3-methyl-4-[4-(3-phenyl-ureido)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (40 mg, 0.09 mmol) in ethanol (2 mL) and THF (3 mL) was added a solution of sodium hydroxide (262 uL, 1.0 N) at room temperature. The resulting mixture was stirred for 5 hours. Then, the solvents were removed under vacuum and the residue was diluted with water (10 mL) and acidified with 1.0 N hydrochloric acid. The mixture was allowed to stand for 3 h, then the solid was filtered off and air-dried to afford {6-chloro-3-methyl-4-[4-(3-phenyl-ureido)-phenyl]-naphthalen-2-yl}-acetic acid (37 mg, 95%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.50 (s, 1 H), 8.86 (s, 1 H), 8.77 (s, 1 H), 7.94 (d, J=8.8 Hz, 1 H), 7.84 (s, 1 H), 7.64 (d, J=8.2 Hz, 2 H), 7.41-7.58 (m, 3 H), 7.30 (t, J=7.8 Hz, 2 H), 7.19 (d, J=1.2 Hz, 1 H), 7.15 (d, J=8.5 Hz, 2 H), 6.99 (t, J=7.2 Hz, 1 H), 3.85 (s, 2 H), 2.12 (s, 3 H). HRMS calcd. for C26H22ClN2O3 [(M+H)+] 445.1314, obsd. 445.1311.

Workup

  1. customThen, the solvents were removed under vacuum
  2. additionthe residue was diluted with water (10 mL)
  3. waitto stand for 3 h
  4. filtrationthe solid was filtered off
  5. customair-dried

Sources & evidence

ORD record
ord-98e637dcead34d8a891c9f30aa261cba
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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