Sodium Hydroxide → 2-(5-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 246774Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:9]2=[N:10][C:11]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=4)[N:16]([CH3:27])[N:15]=3)=[CH:12][N:13]=[C:8]2[N:7](COC(=O)C(C)(C)C)[CH:6]=1)=[O:4].[OH-].[Na+]>O1CCOCC1.O>[CH3:26][S:23]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:27])[N:15]=[C:14]2[C:11]1[N:10]=[C:9]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][NH:7][C:8]2=[N:13][CH:12]=1)(=[O:25])=[O:24]

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of methyl2-(1-methyl-5-(methylsulfonyl)-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (80 mg, 0.16 mmol) in dioxane/water (6 mL/4 mL) was added NaOH (100 mg, 2.5 mmol), the reaction mixture was heated to 85° C. with stirring for 4 hours, the dioxane was removed under reduced pressure, the aqueous layer was adjusted to pH=4 with 2 N HCl. The formed precipitate was collected by filtration, washed with water (3 mL) and dried to afford 2-(5-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (40 mg, 67.7%) as an orange solid. LCMS: (M+H)+=372; 1H NMR (300 MHz, DMSO): δ 12.89 (d, 1H, J=2.7 Hz), 12.49 (brs, 1H), 9.47 (s, 1H), 9.08 (s, 1H), 8.50 (d, 2H, J=3.3 Hz), 8.01-7.95 (m, 1H), 4.23 (s, 3H), 3.27 (s, 3H).

Workup

customthe dioxane was removed under reduced pressure
filtrationThe formed precipitate was collected by filtration
washwashed with water (3 mL)
customdried

Sources & evidence

ORD record: ord-c58e7907e78f45f09379f8294724aca5
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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