2-Bromo-4-methylpyridine → HCID 59013758, compound

HRID 907559Notes

Reaction equation

HRID 907559 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=1.BrC1C=C(C)C=CN=1.[F:24][C:25]([F:52])([F:51])[C:26]1[CH:27]=[C:28]([NH:36][C:37]([N:39]2[CH2:44][CH2:43][N:42]([C:45]3[C:49](Cl)=[N:48][S:47][N:46]=3)[CH2:41][CH2:40]2)=[O:38])[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1>C(O)(C)(C)C>[F:52][C:25]([F:24])([F:51])[C:26]1[CH:27]=[C:28]([NH:36][C:37]([N:39]2[CH2:44][CH2:43][N:42]([C:45]3[C:49]([O:15][CH2:14][C:12]4[CH:11]=[CH:10][N:9]=[C:8]([Br:7])[CH:13]=4)=[N:48][S:47][N:46]=3)[CH2:41][CH2:40]2)=[O:38])[CH:29]=[C:30]([C:32]([F:33])([F:35])[F:34])[CH:31]=1

Participants

6

Reactant 4

HCID 27340872-Bromo-4-methylpyridineHCID 14512957(2-Bromopyridin-4-yl)methanolHCID 23665647Potassium tert-butoxideHCID 590137964-(4-Chloro-[1,2,5]thiadiazol-3-yl)-piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)amide

Product 1

HCID 59013758HCID 59013758, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of potassium t-butoxide (0.070 g, 0.63 mmol) and t-butanol (0.5 mL) was added dropwise with stirring (2-bromo-pyridin-4-yl)-methanol (0.078 g, 0.42 mmol, prepared in the similar fashion as Example 16a from 2-Bromo-4-methyl-pyridine), followed by 4-(4-chloro-[1,2,5]thiadiazol-3-yl)-piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide (0.100 g, 0.21 mmol; prepared in Example 10b). The mixture was stirred at room temperature overnight. LC/MS analysis indicated formation of the desired product. The mixture was concentrated in vacuo, and the crude product was purified on preparative HPLC to afford N-[3,5-bis(trifluoromethyl)phenyl]-4-(4-{[(2-bromopyridin-4-yl)methyl]oxy}-1,2,5-thiadiazol-3-yl)piperazine-1-carboxamide (13 mg, 10% yield). 1H NMR (CDCl3) 8.40 (s, 1H), 7.95 (s, 2H), 7.45 (s, 2H), 7.25 (m, 1H), 6.6 (s, 1H), 5.45 (m, 2H), 3.6 (m, 4H), 1.6 (m, 4H) ppm.

Sources & evidence

ORD record
ord-2f5b76120a214cfbbc659c37625503eb
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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