7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid → 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1394897Notes

Reaction equation

[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][C:18]=4[N:9]3[CH2:8][CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>C1COCC1.CO.[OH-].[Na+]>[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][C:18]=4[N:9]3[CH2:8][CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[CH:17][C:18]=4[N:9]3[CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-fluoro-6-(4-morpholinylcarbonyl)-, methyl ester (125 mg, 0.249 mmol) in THF/Methanol mixture (2.0 mL/2.0 mL), 2N NaOH solution (1.0 mL) was added. The reaction mixture was heated at 90° C. under microwave condition for 10 min. Then it was concentrated and acidified with 1N HCl solution. Extracted with ethyl acetate (2×20 mL) and the organic layers were combined, dried (MgSO4) and concentrated. The residue was purified by prep HPLC to give 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-fluoro-6-(4-morpholinylcarbonyl)- (12 mg, 10% yield) and 5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-fluoro-6-(4-morpholinylcarbonyl)- (15 mg, 12% yield).

Workup

concentrationThen it was concentrated
extractionExtracted with ethyl acetate (2×20 mL)
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified by prep HPLC

Sources & evidence

ORD record: ord-fa23e44cc9b1475b8796b08fce3f3e7c
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348425B2

Reaction notes

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