HCID 57747318, compound → HCID 44124457, compound

HRID 386625Notes

Reaction equation

HRID 386625 reaction equation
[CH3:1][C:2]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[CH:32]=[C:31]([CH3:41])[C:3]=1[O:4][C:5]1[C:6]2[N:29]([CH3:30])[CH:28]=[CH:27][C:7]=2[N:8]=[C:9]([N:11]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=2)C(=O)OC(C)(C)C)[N:10]=1>C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[CH:34]=[C:33]([C:35]2[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=2)[CH:32]=[C:31]([CH3:41])[C:3]=1[O:4][C:5]1[C:6]2[N:29]([CH3:30])[CH:28]=[CH:27][C:7]=2[N:8]=[C:9]([NH:11][C:19]2[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[CH:23][CH:24]=2)[N:10]=1

Participants

3

Reactant 1

HCID 57747318HCID 57747318, compound

Product 1

HCID 44124457HCID 44124457, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(2,6-dimethyl-4-(pyridin-4-yl)phenoxy)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl-4-cyanophenylcarbamate was treated with TFA (10 mL) at 25° C. for 2 h. TFA was evaporated, the obtained residue dissolved in EtOAc, and extracted with saturated aqueous NaHCO3 (×2). The organic layer was collected, concentrated, and the product purified by chromatography (SiO2, 1:4 hexanes/EtOAc) to give the title compound as a solid (277 mg, 100%). 1H NMR (400 MHz, CDCl3-CD3OD (5:1), 25° C.) δ 8.67 (bs, 2H), 7.63 (m, 3H), 7.50 (s, 2H), 7.43 (d, J=8.8 Hz, 2H), 7.32 (d, J=3.0 Hz, 1H), 7.26 (d, J=8.7 Hz, 2H), 6.43 (d, J=2.9 Hz, 1H), 4.16 (s, 3H), 2.27 (s, 6H).

Workup

  1. customTFA was evaporated
  2. dissolutionthe obtained residue dissolved in EtOAc
  3. extractionextracted with saturated aqueous NaHCO3 (×2)
  4. customThe organic layer was collected
  5. concentrationconcentrated
  6. customthe product purified by chromatography (SiO2, 1:4 hexanes/EtOAc)

Sources & evidence

ORD record
ord-77c660090ccc477a908d797bf75abe40
Source dataset
uspto-grants-2013_02
Patent number
US08372852B2

Reaction notes

Loading…