Ethanol → HCID 66812045, compound

HRID 1097418Notes

Reaction equation

HRID 1097418 reaction equation
C[CH2:2][OH:3].[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:35]=[C:15]3[N:16]=[CH:17][CH:18]=[C:19]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH:27]([F:29])[F:28])=[C:22]([O:30][CH2:31][CH:32]5[CH2:34][CH2:33]5)[CH:21]=4)[N:14]3[N:13]=2)=[CH:8][N:7]=1)#[N:5].C[Si](Cl)(C)C.C([O-])(O)=[O:42].[Na+]>>[CH3:2][O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:35]=[C:15]3[N:16]=[CH:17][CH:18]=[C:19]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH:27]([F:28])[F:29])=[C:22]([O:30][CH2:31][CH:32]5[CH2:33][CH2:34]5)[CH:21]=4)[N:14]3[N:13]=2)=[CH:8][N:7]=1)=[O:42].[CH:32]1([CH2:31][O:30][C:22]2[CH:21]=[C:20]([C:19]3[N:14]4[N:13]=[C:12]([C:9]5[CH:10]=[CH:11][C:6]([C:4]([NH2:5])=[O:3])=[N:7][CH:8]=5)[N:35]=[C:15]4[N:16]=[CH:17][CH:18]=3)[CH:25]=[CH:24][C:23]=2[O:26][CH:27]([F:29])[F:28])[CH2:33][CH2:34]1

Participants

6

Reactant 4

HCID 702EthanolHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 66811752HCID 66811752, compound2×

Product 2

HCID 66811966HCID 66811966, compoundYield 24%HCID 66812045HCID 66812045, compoundYield 40%

Conditions

Temperature
50 °C

Procedure

In EtOH (13 ml, 220 mmol), dissolved was 2-(2-cyano-pyridin-5-yl)-7-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine (Compound 123) (0.12 g, 0.28 mmol), and TMSCl (14 ml, 110 mmol) was slowly added dropwise thereto, and the mixture was stirred at 50° C. To the reaction mixture, NaHCO3(aq) was added, and the mixture was extracted three times with CH2Cl. The extract was washed twice with brine, dried over MgSO4, filtered, and evaporated under reduced pressure to remove solvent. The mixture was purified via silica gel column chromatography (CH2Cl2/MeOH, 100/1) to obtain the desired compound, 5-[7-{3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl}-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]pyridine-2-carboxylic acid methyl ester (Compound 138) (0.05 g, 40%) and 5-[7-{3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl}-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]pyridine-2-carboxamide (Compound 139) (0.03 g, 24%).

Workup

  1. additionwas slowly added dropwise
  2. extractionthe mixture was extracted three times with CH2Cl
  3. washThe extract was washed twice with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto remove solvent
  8. customThe mixture was purified via silica gel column chromatography (CH2Cl2/MeOH, 100/1)

Sources & evidence

ORD record
ord-f5017adcd11547c49668df20bd3fb442
Source dataset
uspto-grants-2012_03
Patent number
US08143262B2

Reaction notes

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