4-Methoxy-alpha-toluenethiol → 4-{[3-(Methyloxy)phenyl]amino}-6-({[4-(methyloxy)phenyl]methyl}thio)-3-quinolinecarboxamide

HRID 230861Notes

Reaction equation

Cl.I[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([NH2:15])=[O:14])=[C:6]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1.CC(C)([O-])C.[K+].[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][SH:40])=[CH:35][CH:34]=1.O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1>CN(C)C=O>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([NH:16][C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([S:40][CH2:39][C:36]4[CH:37]=[CH:38][C:33]([O:32][CH3:31])=[CH:34][CH:35]=4)[CH:4]=3)[N:9]=[CH:8][C:7]=2[C:13]([NH2:15])=[O:14])[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Intermediate 14 (0.020 g), potassium tert-butoxide (0.0061 g) and [4-(methyloxy) phenyl]methanethiol (available from Aldrich) (0.007 ml) were added to a stirred solution of tris(dibenzylidineacetone)dipalladium(0) (0.002 g) and (oxydi-2,1-phenylene)bis (diphenylphosphine) (0.002 g) in N,N-dimethylformamide (1.5 ml), and the mixture was heated under microwave irradiation at 60° C. for 8 min. The solvent was evaporated in vacuo, and the residue purified by Mass Directed Preparative HPLC (Method A) to give the title compound (0.0048 g).

Workup

customThe solvent was evaporated in vacuo
customthe residue purified by Mass Directed Preparative HPLC (Method A)

Sources & evidence

ORD record: ord-28ee6ea5069f418aae92f3f69428b049
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566786B2

Reaction notes

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