HCID 68157977, compound → HCID 68157198, compound

HRID 243258Notes

Reaction equation

HRID 243258 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]([CH3:17])[CH3:16])[C:13]2[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:19]([F:22])[CH:20]=[CH:21][C:12]=2[N:11]=1)[CH3:9])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([CH:15]([CH3:16])[CH3:17])[C:13]=2[C:18]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

4

Reactant 1

HCID 68157977HCID 68157977, compound

Product 1

HCID 68157198HCID 68157198, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[(S)-1-(6-Fluoro-1-isopropyl-7-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (0.6 g, 1.5 mmol) was dissolved in 20% TFA in DCM (10 mL). The resulting solution was stirred for 1 h then the mixture was passed through an SCX column. The column was washed with DCM and MeOH to remove non-basic impurities and the product was then eluted with 2M NH3 in MeOH. The product fractions were concentrated to give a yellow solid (0.34 g, 76%). 1H NMR (CDCl3, 400 MHz): δ 8.77 (1H, d, J=6.1 Hz), 7.85 (1H, td, J=10.5, 2.4 Hz), 7.69 (1H, dd, J=11.4, 6.4 Hz), 7.57 (1H, d, J=10.8 Hz), 7.38 (1H, dd, J=9.8, 6.9 Hz), 7.07 (1H, dd, J=13.7, 11.6 Hz), 4.35 (1H, q, J=8.7 Hz), 4.03 (1H, sept, J=9.3 Hz), 1.60 (3H, d, J=8.8 Hz), 1.40-1.29 (6H, m)

Workup

  1. washThe column was washed with DCM and MeOH
  2. customto remove non-basic impurities
  3. washthe product was then eluted with 2M NH3 in MeOH
  4. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-02474845627042fd8c059f6da2287e8d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…