2-Chloroquinoline → HCID 67109937, compound

HRID 915764Notes

Reaction equation

[C:1]([O:5][C:6](=[O:29])[CH:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].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.[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:29])[CH:7]([NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[CH:23][C:24]([CH2:27][O:28][C:33]3[N:32]=[CH:31][C:40]4[C:35]([CH:34]=3)=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Step 3C 2-(4′-Hydroxymethyl-biphenyl-4-sulfonylamino)-3-methyl-butyric acid tert-butyl ester (700 mg, 1.68 mmol, 1 equiv), 2-chloroquinoline (1.1 g, 6.7 mmol, 4 equiv) were dissolved in DMF (20 mL) and added with and NaH (202 mg,60% in oil, 5.04 mmol, 3 equiv). The mixture was heat to 100° C. for 2 hrs. After cooling to room temperature, the reaction mixture was quenched with sat. NH4Cl (aq). After stirring for 0.5 h, solid precipitated from the mixture. Solid was collected by filtration and washed with water and dried overnight to produce 793 mg of 2-[4′-(Isoquinolin-3-yloxymethyl)-biphenyl-4-sulfonylamino]-3-methyl-butyric acid tert-butyl ester in 87% yield.

Workup

temperatureAfter cooling to room temperature
customthe reaction mixture was quenched with sat. NH4Cl (aq)
customsolid precipitated from the mixture
filtrationSolid was collected by filtration
washwashed with water
customdried overnight

Sources & evidence

ORD record: ord-51d31d962a374d38aa780dd07bc7b7fa
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268135B2

Reaction notes

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