Sodium Hydroxide → HCID 68328127, compound

HRID 634329Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]3[O:22][C:23]([NH:26][CH:27]([CH3:29])[CH3:28])=[N:24][N:25]=3)[CH:19]=2)[N:14](S(C2C=CC(C)=CC=2)(=O)=O)[CH:13]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]3[O:22][C:23]([NH:26][CH:27]([CH3:29])[CH3:28])=[N:24][N:25]=3)[CH:19]=2)[NH:14][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-fluoro-3-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylbenzamide (250 mg, 0.457 mmol) in 1,4-dioxane (5 mL) was added aq. NaOH (7 M, 5 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 (eluted with 20-80% MeCN in water with 0.1% TFA in each solvent) to give 4-fluoro-3-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)-N-methylbenzamide (23 mg, 12%). MS (ESI, pos. ion) m/z: 394.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 11.90 (s, 1H), 8.56 (d, 1H, J=4.8 Hz), 8.16 (dd, 1H, J=7.2, 2.4 Hz), 8.01 (s, 1H), 7.81-7.84 (m, 2H), 7.70 (dd, 1H, J=8.8, 1.2 Hz), 7.60-7.63 (m, 2H), 7.46 (dd, 1H, J=10.4, 8.8 Hz), 3.68-3.76 (m, 1H), 2.81 (d, 3H, J=4.4 Hz), 1.20 (d, 6H, J=6.8 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 (
washeluted with 20-80% MeCN in water with 0.1% TFA in each solvent)

Sources & evidence

ORD record: ord-e546d9268f4947bf84bd239d6b4c7f2a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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