Sodium Hydroxide → 3-(3-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenylamino)-3-oxopropanoic acid

HRID 347479Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the above crude ethyl 3-(3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenylamino)-3-oxopropanoate (180 mg) in ethanol (10 mL) at 0° C. was added 1 N aq NaOH solution (10 mL). After stirring at 0° C. for 3 h, the reaction was washed with 20 mL of EtOAc. The EtOAc layer was back-extracted with 20 mL of 1 N aq NaOH solution. The combined aqueous solution was acidified to pH with 1 N aq HCl solution. The aqueous layer was extracted with EtOAc (3×30 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude acid which was used without further purification (150 mg). MS(ESI+) m/z 331.1 (M++H)+.

Workup

washthe reaction was washed with 20 mL of EtOAc
extractionThe EtOAc layer was back-extracted with 20 mL of 1 N aq NaOH solution
extractionThe aqueous layer was extracted with EtOAc (3×30 mL)
dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e34075ef758942d6a5f7a8e494451a35
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173031B2

Reaction notes

Loading…