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

Cesium carbonate → 4-((R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine-7-ylamino)-3-trifluoromethyl-N-methylbenzamide

HRID 562510
Notes
Print preview

Reaction equation

HRID 562510 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]3[CH:12]=[N:13][N:14]=[C:7]3[C@@H:6]([CH2:15][CH3:16])[N:5]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:4]=2[N:3]=1.[NH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][CH3:30])=[O:28])=[CH:25][C:24]=1[C:33]([F:36])([F:35])[F:34].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:17]1([N:5]2[C:4]3[N:3]=[C:2]([NH:22][C:23]4[CH:32]=[CH:31][C:26]([C:27]([NH:29][CH3:30])=[O:28])=[CH:25][C:24]=4[C:33]([F:34])([F:35])[F:36])[N:11]=[CH:10][C:9]=3[N:8]3[CH:12]=[N:13][N:14]=[C:7]3[C@H:6]2[CH2:15][CH3:16])[CH2:21][CH2:20][CH2:19][CH2:18]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59389586(R)-7-chloro-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridineHCID 621563944-amino-N-methyl-3-(trifluoromethyl)benzamide

Product 1

HCID 24890611
4-((R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine-7-ylamino)-3-trifluoromethyl-N-methylbenzamide
Yield 46%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (R)-7-chloro-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine (100 mg, 0.329 mmol), 4-amino-3-trifluoromethyl-N-methylbenzamide, palladium acetate (6 mg), cesium carbonate (214 mg, 0.658 mmol) and xanthphos (20 mg) in dioxane (4 ml) was stirred at 150° C. in a microwave for 1 hour. The mixture was diluted with ethyl acetate and washed with aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel eluting with 0-12% methanol/ethyl acetate to give 4-((R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridine-7-ylamino)-3-trifluoromethyl-N-methylbenzamide as a colourless glass (70 mg, 46%).

Workup

  1. washwashed with aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel eluting with 0-12% methanol/ethyl acetate

Sources & evidence

ORD record
ord-75b47ba041b842539fb3255db1462d95
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08067417B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes