tert-Butanol → HCID 59013760, compound

HRID 907556Notes

Reaction equation

HRID 907556 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27](Cl)=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CC(C)([O-])C.[K+].C(O)(C)(C)C.[Cl:42][C:43]1[CH:48]=[C:47]([CH2:49][OH:50])[CH:46]=[CH:45][N:44]=1>CO>[F:29][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([O:50][CH2:49][C:47]4[CH:46]=[CH:45][N:44]=[C:43]([Cl:42])[CH:48]=4)=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 7062237(2-Chloropyridin-4-yl)methanolHCID 23665647Potassium tert-butoxideHCID 59013946HCID 59013946, compound

Product 1

HCID 59013760HCID 59013760, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide (115 mg, 0.254 mmol) and 1M solution of potassium tert-butoxide in tert-butanol (0.80 mL, 0.80 mmol) was added 2-Chloro-4-pyridinemethanol (81.8 mg, 0.568 mmol). The resulting suspension was stirred at room temperature for 15 h. The crude reaction mixture was diluted with methanol and purified by preparative HPLC (50 mM NH4OAc(aq), Acetonitrile system). The product was isolated by lyophilization of pure fractions yielding N-[3,5-bis(trifluoromethyl)phenyl]-4-(3-{[(2-chloropyridin-4-yl)methyl]oxy}pyrazin-2-yl)piperazine-1-carboxamide (29.9 mg, 21% yield). 1H NMR (CDCl3) 8.41 (d, 1H), 7.91 (s, 2H), 7.82 (d, 1H), 7.61 (d, 1H), 7.54 (s, 1H), 7.39 (s, 1H), 6.70 (s, 1H), 5.47 (s, 2H), 3.70-3.65 (m, 8H) ppm.

Workup

  1. customThe crude reaction mixture
  2. custompurified by preparative HPLC (50 mM NH4OAc(aq), Acetonitrile system)
  3. customThe product was isolated by lyophilization of pure fractions

Sources & evidence

ORD record
ord-b07c40a2d0f34e04a77d5f45db987fd8
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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