Hydrochloric Acid → HCID 67360181, compound

HRID 2065680Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11].Cl[C:32]1[C:41]([C:42]([OH:44])=[O:43])=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([Cl:45])[CH:38]=2)[N:33]=1.C([O-])([O-])=O.[K+].[K+].Cl>CS(C)=O.O>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([O:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][C@H:9]([NH:8][C:32]3[C:41]([C:42]([OH:44])=[O:43])=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[C:37]([Cl:45])[CH:38]=4)[N:33]=3)[C:10]([OH:12])=[O:11])=[CH:15][CH:16]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of trifluoroacetic acid salt of (S)-2-amino-3-[4-(quinolin-4-yloxy)-phenyl]-propionic acid (0.296 g, 0.7 mmol), 2,6-dichloroquinoline-3-carboxylic acid (0.16 g, 0.66 mmol) and K2CO3 (0.46 g, 3.3 mmol) in dry DMSO (1 mL) is stirred for 13 h in a closed Pierce reaction vial at 100° C. temperature. After cooling the reaction mixture is diluted with water (25 mL), acidified with 2N aqueous HCl till pH 3, and the precipitated solid is collected on filter. The crude product is washed with water and recrystallized from DMF/EtOH (0.5 mL/0.5 mL) mixture to give the title compound as a yellow solid (0.14 g, 41%).

Workup

temperatureAfter cooling the reaction mixture
customthe precipitated solid is collected
filtrationon filter
washThe crude product is washed with water
customrecrystallized from DMF/EtOH (0.5 mL/0.5 mL) mixture

Sources & evidence

ORD record: ord-274a86d005e449d2af39a08b391a7f52
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288549B2

Reaction notes

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