Hydrochloric Acid → 2-{1-Carboxy-2-[4-(quinolin-4-ylamino)-phenyl]-ethylamino}-6-chloro-quinoline-3-carboxylic acid

HRID 2065674Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.O.O.Cl.Cl.[NH2:20][CH:21]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1)[C:22]([OH:24])=[O:23].C([O-])([O-])=O.[K+].[K+].Cl>CS(C)=O.O>[C:22]([CH:21]([NH:20][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1)[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]=[CH:35][CH:34]=2)=[CH:28][CH:27]=1)([OH:24])=[O:23]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2,6-dichloro-quinoline-3-carboxylic acid (0.17 g, 0.7 mmol), 2-amino-3-[4-(quinolin-4-ylamino)-phenyl]propionic acid dihydrochloride dihydrate (0.291 g, 0.7 mmol) and K2CO3 (0.507 g, 3.7 mmol) in DMSO (1.5 mL) is stirred at 110° C. temperature for 24 h in a Pierce reaction vial. After cooling the reaction mixture is diluted with water (10 mL) and acidified with 2N aqueous HCl till pH ˜3. The precipitated solid is collected on filter and washed with water to give the title compound (0.3 g, 84%) as yellow solid.

Workup

customin a Pierce reaction vial
temperatureAfter cooling the reaction mixture
customThe precipitated solid is collected
filtrationon filter
washwashed with water

Sources & evidence

ORD record: ord-f60ae66e9e87407994d73fdf8680c38e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288549B2

Reaction notes

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