Potassium Hydroxide → 5-Fluoro-2-[2-(1-methylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)-benzoylamino]benzoic acid

HRID 644228Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of methyl 5-fluoro-2-[2-(1-methylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]benzoate (7.8 g, 17 mmol) in EtOH (100 mL) and water (100 mL) was treated with KOH (4.8 g, 85 mmol) and stirred at 70° C. for 1 hour. The reaction was concentrated under vacuum, quenched with glacial acetic acid (5.1 g), and allowed to stand at ambient temperature for crystallization. The solid was filtered to recover 7.4 g (98%).

Workup

concentrationThe reaction was concentrated under vacuum
customquenched with glacial acetic acid (5.1 g)
customto stand at ambient temperature for crystallization
filtrationThe solid was filtered
customto recover 7.4 g (98%)

Sources & evidence

ORD record: ord-29111d7396b846a0b16758995c05629b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700628B2

Reaction notes

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