5-Amino-3-methylisoxazole → 4-(6-Fluoro-1H-indazol-5-yl)-3,6-dimethyl-4,7-dihydroisoxazolo[5,4-b]pyridine-5-carbonitrile

HRID 1521791Notes

Reaction equation

HRID 1521791 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1/[CH:11]=[C:12](/[C:15](=O)[CH3:16])\[C:13]#[N:14].[CH3:18][C:19]1[CH:23]=[C:22]([NH2:24])[O:21][N:20]=1>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH:11]1[C:12]([C:13]#[N:14])=[C:15]([CH3:16])[NH:24][C:22]2[O:21][N:20]=[C:19]([CH3:18])[C:23]1=2

Participants

3

Reactant 2

HCID 845905-Amino-3-methylisoxazoleHCID 66616240(2E)-2-[(6-fluoro-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile

Product 1

HCID 1359859984-(6-Fluoro-1H-indazol-5-yl)-3,6-dimethyl-4,7-dihydroisoxazolo[5,4-b]pyridine-5-carbonitrile

Procedure

100 mg (0.44 mmol) (2E)-2-[(6-fluoro-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 13A) were treated with 3-methyl-1,2-oxazol-5-amine following the procedure described in Example 2. The crude material was purified by preparative RP-HPLC (methanol/water+0.1% TFA gradient) to yield 55 mg (41% of th.) of the racemic title compound.

Workup

  1. customThe crude material was purified by preparative RP-HPLC (methanol/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-0d047b3a98d946f6b3e51ac472b9a281
Source dataset
uspto-grants-2015_07
Patent number
US09073939B2

Reaction notes

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