Sodium Hydroxide → 2-[4-(2-cyano-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid

HRID 2381353Notes

Reaction equation

C[O:2][C:3](=[O:27])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>CO>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][C:14]1[CH:13]=[N:12][N:11]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([OH:27])=[O:2])[C:16](=[O:17])[CH:15]=1)#[N:26]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-[4-(2-cyano-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester (30 g, 82 mmol) in methanol (30 mL) was treated with a 4N aqueous sodium hydroxide solution (26.5 mL, 106 mmol) and stirred at 25° C. for 18 h. At this point, the reaction was concentrated in vacuo and then diluted with water. The translucent aqueous solution was acidified to pH 4-5 with a 1N aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration, rinsed and dried in vacuo to afford 2-[4-(2-cyano-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid (12.0 g, 41%) as a white solid; ESI-MS 354 [M+H+]; HPLC: >96% (purity). 1H-NMR (300 MHz, CDCl3) δ 9.65 (s, 1H), 7.93 (s, 1H), 7.68-7.78 (m, 2H), 7.43-7.45 (m, 1H), 7.28-7.31 (m, 1H), 6.07 (s, 1H), 5.51-5.56 (m, 1H), 2.29-2.39 (m, 1H), 2.05-2.15 (m, 1H), 1.44-1.82 (m, 7H), 1.09-1.22 (m, 2H).

Workup

concentrationAt this point, the reaction was concentrated in vacuo
additiondiluted with water
filtrationThe resulting precipitate was collected by filtration
washrinsed
customdried in vacuo

Sources & evidence

ORD record: ord-268af59971c444919b0799504e6363c8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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