Trifluoroacetic acid → HCID 58405310, compound

HRID 44851Notes

Reaction equation

HRID 44851 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]1([N:13]2[C:22]3[N:21]=[C:20]([C:23]4[CH:28]=[CH:27][N:26]=[CH:25][C:24]=4[NH:29]C(=O)OC(C)(C)C)[N:19]=[CH:18][C:17]=3[N:16]([CH3:37])[C:15](=[O:38])[C@H:14]2[CH2:39][CH3:40])[CH2:12][CH2:11][CH2:10][CH2:9]1>C(Cl)Cl>[NH2:29][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:23]=1[C:20]1[N:19]=[CH:18][C:17]2[N:16]([CH3:37])[C:15](=[O:38])[C@@H:14]([CH2:39][CH3:40])[N:13]([CH:8]3[CH2:12][CH2:11][CH2:10][CH2:9]3)[C:22]=2[N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58405528HCID 58405528, compound

Product 1

HCID 58405310HCID 58405310, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Three mL of TFA was added to a solution of (R)-tert-butyl 4-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)pyridin-3-ylcarbamate (Example 92, 760 mg) in 3 mL of DCM. The mixture was stirred for 4 h at rt, and the solvent was removed under reduced pressure. Aqueous Na2CO3 was added and extracted with EtOAc. The organic layer was dried with Na2SO4, concentrated and the residue was purified by silica column to give the title compound. LCMS (0.05% TFA): 353.0 m/z (M+H)+; 1H-NMR (CDCl3, 500 MHz): δ: 8.17 (s, 1H), 8.08 (d, 1H, J=5 Hz), 7.99 (d, 1H, J=5 Hz), 7.94 (s, 1H), 6.23 (s, 2H), 4.48 (m, 1H), 4.32 (m, 1H), 3.39 (s, 3H), 2.0-1.69 (m, 10H), 0.88 (t, 3H, J=7.5 Hz).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionAqueous Na2CO3 was added
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by silica column

Sources & evidence

ORD record
ord-8480fff61734432fb2841d2366cefbe0
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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