Potassium Carbonate → HCID 10407118, compound

HRID 1455501Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[CH:7][CH:8]=2)[N:3]=1.[C:17]([O:21][C:22](=[O:28])[NH:23][CH2:24][CH2:25][CH2:26][NH2:27])([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:17]([O:21][C:22]([NH:23][CH2:24][CH2:25][CH2:26][NH:27][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[CH:7][CH:8]=2)[N:3]=1)=[O:28])([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 2-Chloro-7-methoxy-quinoline-3-carboxylic acid (60 mg, 0.22 mmol), (3-Amino-propyl)-carbamic acid tert-butyl ester (77 mg, 0.44 mmol), Potassium carbonate (73 mg, 0.46 mmol), and Molecular sieve-4A (300 mg) in dry DMSO (4 ml) was heated at 100° C. for over night. The reaction mixture was purified by chromatography on SCX column using MeOH as eluent and 2-(3-tert-Butoxycarbonylamino-propylamino)-7-methoxy-quinoline-3-carboxylic acid was obtained as white solid after recrystallization from CH2Cl2 and Hexane; 70 mg (85%).

Workup

customThe reaction mixture was purified by chromatography on SCX column

Sources & evidence

ORD record: ord-ebc2d85e6210435fa2edcefb1a66d31d
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482455B2

Reaction notes

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