HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → HCID 178440650, compound

HRID 1412544
Notes
Print preview

Reaction equation

HRID 1412544 reaction equation
[CH2:1]([C:5]1[N:10]2[N:11]=[CH:12][CH:13]=[C:9]2[N:8]([C@H:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]2)[C:7](=[O:21])[C:6]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[C:31]#[N:32])=[N:27][CH:28]=1)[CH2:2][CH2:3][CH3:4].[N+](=[CH:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[N-].C(OCC)(=O)C.O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:43]([O:42][C:40](=[O:41])[CH2:39][O:20][C@H:17]1[CH2:18][CH2:19][C@H:14]([N:8]2[C:7](=[O:21])[C:6]([CH2:22][C:23]3[CH:28]=[N:27][C:26]([C:29]4[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=4[C:31]#[N:32])=[CH:25][CH:24]=3)=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:10]3[N:11]=[CH:12][CH:13]=[C:9]23)[CH2:15][CH2:16]1)[CH3:44]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12192Ethyl diazoacetateHCID 178440648HCID 178440648, compound

Product 1

HCID 178440650HCID 178440650, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 168478
Rhodium acetate
Catalyst
HCID 1140TolueneSolvent

Procedure

To a solution of 2-(5-{[7-butyl-4-(trans-4-hydroxycyclohexyl)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}pyridin-2-yl)benzonitrile (0.48 g) and rhodium acetate (dimer, 0.044 g) in toluene (5 mL) was added dropwise ethyl diazoacetate (0.52 mL), and the mixture was stirred for 5 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.26 g, 47%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f3abeeef805b49ffa1b4373a28835e4b
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921379B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes