Tert-Butylamine → HCID 49869798, compound

HRID 1631311Notes

Reaction equation

HRID 1631311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23](O)=[O:24])=[C:16]2[N:15]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:50]([NH2:54])([CH3:53])([CH3:52])[CH3:51].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[C:50]([NH:54][C:23]([C:22]1[CH:21]=[N:20][N:17]2[CH:18]=[CH:19][C:14]([N:10]3[CH2:11][CH2:12][CH2:13][C@@H:9]3[C:3]3[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=3[F:1])=[N:15][C:16]=12)=[O:24])([CH3:53])([CH3:52])[CH3:51]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66847716(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 49869798HCID 49869798, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation C, 20.0 mg, 0.058 mmol) and HATU (24.3 mg, 0.064 mmol) in dry DMF (0.4 mL) was added tert-butyl amine (12.7 mg, 0.174 mmol) followed by diisopropylethylamine (22.5 mg, 0.174 mmol). The mixture was stirred under an atmosphere of N2 for 18 hours and was added to H2O (3 mL) and mixed. The mixture was extracted with EtOAc and combined extracts were washed with 1M HCl, H2O, saturated NaHCO3 and dried over MgSO4. The solution was eluted through a SPE SiOH column eluting first with 50% EtOAc-hexanes then with EtOAc. The EtOAc pool was concentrated and the residual colorless glass was treated with hexanes give a white suspension. The hexanes were removed, and the solid was washed with hexanes and dried in vacuum to afford the title compound as a white solid (20 mg, 90%). MS (apci) m/z=400.1 (M+H).

Workup

  1. additionmixed
  2. extractionThe mixture was extracted with EtOAc
  3. washwere washed with 1M HCl, H2O, saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. washThe solution was eluted through a SPE SiOH column
  6. washeluting first with 50% EtOAc-hexanes
  7. concentrationThe EtOAc pool was concentrated
  8. additionthe residual colorless glass was treated with hexanes
  9. customgive a white suspension
  10. customThe hexanes were removed
  11. washthe solid was washed with hexanes
  12. customdried in vacuum

Sources & evidence

ORD record
ord-2822815a595f4bc09e6e6d18b16fbb3d
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

Loading…