Hydrochloric Acid → 2-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-isonicotinic acid

HRID 2267035Notes

Reaction equation

[OH-].[Li+].C[O:4][C:5](=[O:34])[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([OH:30])[C:22]=3[CH2:31][CH2:32][CH3:33])[CH:14]=2)[CH:7]=1.O.Cl>O1CCCC1>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:15]2[CH:14]=[C:13]([NH:12][C:8]3[CH:7]=[C:6]([CH:11]=[CH:10][N:9]=3)[C:5]([OH:34])=[O:4])[CH:18]=[CH:17][CH:16]=2)=[C:22]([CH2:31][CH2:32][CH3:33])[C:23]=1[OH:30])(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

Add 1M aqueous lithium hydroxide (2.14 mL, 2.14 mmol) to a solution of 2-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-isonicotinic acid methyl ester (282 mg, 0.649 mmol) in tetrahydrofuran (20 mL):water (20 mL) and stir. Heat to 80° C. After 1 hour, pour reaction into 1N aqueous hydrochloric acid (50 mL) and filter the resulting precipitate to yield the title compound as a yellow solid (59 mg, 22%): 1H NMR (DMSO-d6) δ 0.86 (t, 3H), 1.52 (sextet, 2H), 2.57 (s, 3H), 2.63 (t, 2H), 5.25 (s, 2H), 6.72 (d, 1H), 6.99 (d, 1H), 7.13 (d, 1H), 7.30 (t, 1H), 7.37 (s, 1H), 7.56 (d, 1H), 7.80 (d, 1H), 7.91 (s, 1H), 8.28 (d, 1H), 9.37 (s, 1H), 12.85 (s, 1H), 13.44 (bs, 1H); MS (esi negative) m/z (rel intensity) 419 (100).

Workup

additionpour
filtrationfilter the resulting precipitate

Sources & evidence

ORD record: ord-024c35a4b64e4aa98cba718457d81374
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858646B2

Reaction notes

Loading…