Hydrochloric Acid → HCID 178450279, compound

HRID 2271766Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[CH:24]=[C:23]([Cl:25])[C:22]([OH:26])=[C:21]([Cl:27])[CH:20]=4)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[CH2:4][CH2:3]1.[ClH:33]>C1COCC1>[ClH:25].[ClH:33].[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([Cl:27])[C:22]([OH:26])=[C:23]([Cl:25])[CH:24]=4)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:28](=[O:32])[CH:29]([CH3:30])[CH3:31])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 1-{4-[trans-4-Aminocyclohexylamino]-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl}-2-methylpropan-1-one (3.0 g, 6.4 mmol) in THF (50 mL) was added 3 M HCl (30 mL) and the reaction mixture was heated at 60° C. for 2 h. The reaction mixture was cooled and the precipitate was filtered to afford the desired product (4.7 g, 92%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.18 (bs, 1H), 8.49 (bs, 1H), 8.27 (d, J=8.8 Hz, 1H), 7.02 (d, J=8.8 Hz, 1H), 7.75 (bs, 2H), 4.54 (bs, 1H), 3.80-3.69 (m, 1H), 2.52 (bs, 2H), 2.29-2.22 (m, 2H), 1.94-1.81 (m, 2H), 1.75-1.62 (m, 2H), 1.24 (d, J=6.8 Hz, 6H); ESI MS m/z 472 [C25H27C12N3O2+H]+.

Workup

temperatureThe reaction mixture was cooled
filtrationthe precipitate was filtered

Sources & evidence

ORD record: ord-09e5da359c16498bb6ea37a1e4fae833
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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