Hydrochloric Acid → 6-Cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)-4-(indol-5-ylamino)quinoline hydrochloride

HRID 2222391Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]3)=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[CH:30]2.Cl>CC(O)CCC.C(O)(C)C>[ClH:1].[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]1)[N:5]=[CH:4][CH:3]=[C:2]2[NH:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[CH:30]2)#[N:13]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 4-chloro-6-cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)quinoline (80 mg, 0.21 mmol) and 5-aminoindole (33 mg, 0.25 mmol) in 2-pentanol (2.5 ml) containing 6.2N HCl in isopropanol (40 μl) was heated at 120° C. for 3 hours. After cooling, the solid was collected by filtration, washed with isopropanol followed by ether and dried under vacuum to give 6-cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)-4-(indol-5-ylamino)quinoline hydrochloride (104 mg, 90%).

Workup

temperatureAfter cooling
filtrationthe solid was collected by filtration
washwashed with isopropanol
customdried under vacuum

Sources & evidence

ORD record: ord-470645d8c49b497c9ade6c2107e93537
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371765B2

Reaction notes

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