Sodium Hydroxide → HCID 68328727, compound

HRID 634332Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[O:21][C:22]([NH:25][CH:26]([CH3:28])[CH3:27])=[N:23][N:24]=3)[CH:18]=2)[N:13](S(C2C=CC(C)=CC=2)(=O)=O)[CH:12]=1)[C:5]([NH2:7])=[O:6].[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[O:21][C:22]([NH:25][CH:26]([CH3:28])[CH3:27])=[N:23][N:24]=3)[CH:18]=2)[NH:13][CH:12]=1)[C:5]([NH2:7])=[O:6]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-fluoro-4-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)benzamide (200 mg, 0.375 mmol) in 1,4-dioxane (3.75 mL) was added aq. NaOH (7 M, 3.75 mL) and the reaction was heated at 90° C. for 1 h. The reaction was then quenched with water to get a precipitate. The precipitate was filtered and washed with water (2×100 mL) and dried. The crude product was purified with preparative HPLC (eluting with 20-80% ACN in water with 0.1% TFA in each solvent) to give 3-fluoro-4-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)benzamide (65 mg, 46%). MS (ESI, pos. ion) m/z: 380.1 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.07 (brs, 2H), 7.74-7.83 (m, 4H), 7.51-7.69 (m, 4H), 3.65-3.75 (m, 1H), 1.19 (d, 6H, J=6.6 Hz).

Workup

customThe reaction was then quenched with water
customto get a precipitate
filtrationThe precipitate was filtered
washwashed with water (2×100 mL)
customdried
customThe crude product was purified with preparative HPLC (
washeluting with 20-80% ACN in water with 0.1% TFA in each solvent)

Sources & evidence

ORD record: ord-ee4e4c08b21949bdb5f190b7c6a34706
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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