Cesium carbonate → HCID 86711943, compound

HRID 1475252Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][CH3:5].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:12][C:13]1[N:17]([CH2:18][C:19]2[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=2)[N:16]=[C:15]([C:26]2[S:27][CH:28]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=3)[N:30]=2)[N:14]=1>CS(C)=O>[CH3:5][O:4][CH2:3][CH2:2][O:25][C:21]1[CH:20]=[C:19]([CH2:18][N:17]2[C:13]([CH3:12])=[N:14][C:15]([C:26]3[S:27][CH:28]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([O:37][C:38]([F:39])([F:41])[F:40])=[CH:33][CH:32]=4)[N:30]=3)=[N:16]2)[CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-bromo-2-methoxyethane (3.2 mg, 0.023 mmol), Cs2CO3 (9.4 mg, 0.029 mmol) and 3-((5-methyl-3-(4-(4-(trifluoromethoxy)phenyl)thiazol-2-yl)-1H-1,2,4-triazol-1-yl)methyl)phenol (5.0 mg, 0.012 mmol; synthesized in analogous manner to Example 59, using 2-(5-methyl-1H-1,2,4-triazol-3-yl)-4-(4-(trifluoromethoxy)phenyl)thiazole, Example 87, Step 4) in DMSO (0.2 ml) was stirred at 50° C. for 20 minutes. The mixture was purified by prep-HPLC to give the title compound; MS (ES+) C23H21F3N4O3S requires: 474. found: 475 [M+H]+.

Workup

customThe mixture was purified by prep-HPLC

Sources & evidence

ORD record: ord-815af5dffe5c4a3abec06a107e12eb71
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018380B2

Reaction notes

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