4-Aminopyridine → HCID 178520577, compound

HRID 870575Notes

Reaction equation

HRID 870575 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][NH:19][CH2:18][CH2:17][C:15]=2[N:16]=1.[N:21]1[N:22]=[C:23]([CH2:26][CH2:27][CH2:28][CH2:29][C:30](O)=[O:31])[NH:24][CH:25]=1.N1C=CC(N)=CC=1.Cl.CN(C)CCCN=C=NCC>O.C(OCC)(=O)C.ClCCl.CN(C)C=O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][N:19]([C:30](=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][C:23]3[NH:24][CH:25]=[N:21][N:22]=3)[CH2:18][CH2:17][C:15]=2[N:16]=1

Participants

9

Reactant 4

HCID 17274-AminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86726522N-(indan-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amineHCID 178525395HCID 178525395, compound

Product 1

HCID 178520577HCID 178520577, compoundYield 27%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.189 g; 1.0 equiv; 0.71 mmoles) to a solution containing 5-(4H-1,2,4-triazol-3-yl)pentanoic acid (0.40 g 1.0 equiv; 0.71 mmoles), followed by dimethylformamide (2 mL). Stir the resulting solution at room temperature until homogeneous. Add 4-pyridinamine, N,N-dimethyl-(0.017 g; 0.2 equiv; 0.141 mmoles), and cool the solution to 0° C. Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.204 g; 1.5 equiv; 1.06 mmoles) in one portion. Allow the mixture to warm to room temperature and stir for 30 minutes. Add dichloromethane (2 mL), heat to 40° C., and stir for 24 hours. Dilute with 250 mL water and then 50 mL ethyl acetate. Extract the mixture with ethyl acetate (5×25 mL). Wash the combined organic extracts with brine (10 mL). Dry the organics over magnesium sulfate, filter, concentrate, and purify via column chromatography (hexanes to 12% methanol in ethyl acetate) to give 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-5-(4H-1,2,4-triazol-3-yl)pentan-1-one (0.08 g; 27% yield) as a white foam: MS (m/z): 418 (M+1).

Workup

  1. temperatureAllow the mixture to warm to room temperature
  2. stirringstir for 30 minutes
  3. stirringstir for 24 hours
  4. extractionExtract the mixture with ethyl acetate (5×25 mL)
  5. washWash the combined organic extracts with brine (10 mL)
  6. dry with materialDry the organics over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify via column chromatography (hexanes to 12% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-0e121594c89f4337903210047deb8237
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

Loading…