Sodium Hydroxide → 6-chloro-5-{4-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}-1H-indole-3-carboxylic acid

HRID 338353Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13]C)=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][C:26]2=[O:31])=[CH:17][CH:16]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][C:26]2=[O:31])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 6-chloro-5-{4-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}-1H-indole-3-carboxylate (55 mg, 0.22 mmol) in methanol (8 mL) was added 1.0M aq. NaOH (2.0 mL, 2.0 mmol). The mixture was stirred at 70° C. for 24 hours. The mixture was adjusted to pH 7 and purified by reverse phase HPLC to give the title compound as a white solid (5 mg, 9% yield). MS (ES+) 429.1 (M+H)+. 1H NMR (400 MHz, CD3OD): δ 7.90 (m, 2H), 7.5 (s, 1H), 7.29 (d, 2H), 6.92 (d, 2H), 4.05 (m, 4H), 3.83 (t, 2H), 3.58 (t, 2H), 3.42 (t, 2H), 2.05 (m, 2H).

Workup

custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-98d1852859e241c396abef59bc50c90b
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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