Sodium Hydroxide → HCID 9867412, compound

HRID 381760Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19]([C:24]2[C:25](=[O:34])[NH:26][C:27]4[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:18]3)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[O:34]=[C:25]1[C:24]([C:19]2[NH:20][C:21]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:14][CH2:13][CH2:12][N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[CH:23][CH:22]=3)=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26]1

Participants

Conditions

Temperature: 50 °C

Procedure

1-(2-{[2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indol-5-yl]oxy}ethyl)-4-piperidinecarboxylic acid ethyl ester (4-1, 138 mg, 0.30 mmol, 1 equiv) was dissolved in MeOH (20 mL). 1 N NaOH (6 mL, 20 equiv) was added and the solution warmed at 50° C. for 5 h. The reaction was concentrated, and the residue was suspended in 4 mL of water. This suspension was neutralized with 1 N HCl to provide 1-(2-{[2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indol-5-yl]oxy}ethyl)4-piperidinecarboxylic acid (4-2) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ8.45 (s, 1H), 7.74 (d, 1H, J=8 Hz), 7.53 (t, 1H, J=8 Hz), 7.38 (m, 2H), 7.28 (t, 1H, J=8 Hz), 7.19 (s, 1H), 7.16 (s, 1H), 6.88 (dd, 1H, J=9, 2 Hz), 4.34 (t, 2H, J=5 Hz), 3.53 (m, 2H), 3.47 (m, 2 H), 2.42 (m, 1H), 2.11 (m, 2H), 1.95 (m, 2H).

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-5895335f4cb64ebe8390d661c72e6438
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306874B1

Reaction notes

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