2-Chloroquinoline → HCID 66578109, compound

HRID 1529084Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH2:27])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].Cl[C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH:27][C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:32]=4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.181 g, 0.5 mmol) was dissolved in DMF and then sodium hydride (60% in mineral oil, 0.028 g, 0.7 mmol) was added. After 20 minutes 2-chloroquinoline (0.1145 g, 0.7 mmol) was added and the reaction was heated to 60° C. for 3 hours. No product was observed by analytical LCMS so the reaction was heated to 100° C. overnight. After cooling the reaction was submitted to standard aqueous workup to give the title compound.

Workup

temperaturewas heated to 100° C. overnight
temperatureAfter cooling the reaction

Sources & evidence

ORD record: ord-c22cbcbbddb941368c0912b74c3b6c17
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090573B2

Reaction notes

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