Dimethyl Sulfate → HCID 67304695, compound

HRID 1009751Notes

Reaction equation

C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][C:12]1[N:13]=[C:14]([NH:17][C:18](=[O:41])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[C:36]4[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=4)[N:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)[S:15][CH:16]=1.S(OC)(O[CH3:46])(=O)=O>C1COCC1.CN(C=O)C>[CH3:46][N:17]([C:14]1[S:15][CH:16]=[C:12]([CH3:11])[N:13]=1)[C:18](=[O:41])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[C:36]3[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=3)[N:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: -5 °C

Procedure

Under an atmosphere of argon, a 1M solution of lithium hexamethyldisilazane in THF (0.52 ml) was added dropwise to a stirred solution of N-(4-methylthiazol-2-yl)-2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetamide (0.205 g) in DMF (4 ml) that had been cooled to −5° C. After 5 minutes, a solution of dimethyl sulphate (0.049 ml) in DMF (1 ml) was added dropwise and the resultant mixture was stirred at 0° C. for 30 minutes. The mixture was evaporated and the residue was purified by preparative HPLC using a Waters ‘Xterra’ reversed-phase column (5 microns silica) using decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound (0.105 g); 1H NMR: (DMSOd6) 2.29 (d, 3H), 3.73 (s, 3H), 3.93 (s, 3H), 3.95 (s, 3H), 4.17 (s, 2H), 6.5 (d, 1H), 6.82 (s, 1H), 7.52 (d, 2H), 7.4 (s, 1H), 7.42 (d, 2H), 7.5 (s, 1H), 8.49 (d, 1H); Mass Spectrum: M+H+ 450.

Workup

customThe mixture was evaporated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-cc257dba11e34e4882ff23347627e6f2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973164B2

Reaction notes

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