Hydrochloric Acid → (s)-1-(2-Hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

HRID 31125Notes

Reaction equation

[C:1]([CH2:4][N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=3)=[O:18])[C:6]1=[O:7])(O)=[O:2].Cl.C(OCC)(=O)C>B.O1CCCC1>[OH:2][CH2:1][CH2:4][N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=3)=[O:18])[C:6]1=[O:7]

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of (S)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 10) (6 mg) in 1.0 M borane in tetrahydrofuran solution (2 mL) under argon was stirred at 35° C. for 3 h. After cooling to room temperature, 1.0 M aqueous hydrochloric acid (10 mL) and ethyl acetate (10 mL) were added. This mixture was stirred for 3 h before the layers were separated. The organic phase was washed with water (10 mL three times) and evaporated under vacuum. The residue was chromatographed on reverse phase preparative HPLC to isolate the title compound (1.1 mg) and the over-reduction product (S)-1-(2-hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-1,2,3,4-tetrahydroquinoline (0.9 mg). Title compound HPLC/MS [M+H]+, 384.

Workup

temperatureAfter cooling to room temperature
stirringThis mixture was stirred for 3 h before the layers
customwere separated
washThe organic phase was washed with water (10 mL three times)
customevaporated under vacuum
customThe residue was chromatographed on reverse phase preparative HPLC

Sources & evidence

ORD record: ord-9918eb3af82748fca7f061339e6f90e1
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425550B2

Reaction notes

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