Sodium Hydroxide → 4-[6-(5-Chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidin-4-ylamino]-nicotinic acid

HRID 1010847Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

4-[6-(5-Chloro-2-fluoro-phenyl)-3-methyl-isoxazolo[5,4-d]pyrimidin-4-ylamino]-nicotinic acid methyl ester (525 mg) was suspended in methanol (4 ml), 1M sodium hydroxide solution (4 ml) was added, and then heated to 70° C. for 30 min. The methanol was removed under vacuum and the solution was acidified to pH 4 with 6 M hydrochloric acid. The solid was filtered, washed with water and dried in the oven to give 137 mg product.

Workup

customThe methanol was removed under vacuum
filtrationThe solid was filtered
washwashed with water
customdried in the oven

Sources & evidence

ORD record: ord-9cce29f57b184312b2209e3907df1ae4
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977342B2

Reaction notes

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