Trifluoroacetic acid → HCID 11347930, compound

HRID 1180092Notes

Reaction equation

HRID 1180092 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:16][C:15]3[CH2:14][CH2:13][NH:12][C:11](=[O:17])[C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.[CH:25]1([CH:31]=O)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[CH:25]1([CH2:31][NH:1][C:2]2[N:7]=[C:6]([C:8]3[NH:16][C:15]4[CH2:14][CH2:13][NH:12][C:11](=[O:17])[C:10]=4[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 16275Cyclohexanecarboxaldehyde2×HCID 5049666Sodium triacetoxyborohydride2×HCID 11300082HCID 11300082, compound

Product 1

HCID 11347930HCID 11347930, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Amino-pyrimidin-4-yl)-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (140 mg, 0.61 mmol), trifluoroacetic acid (565 μl, 7.33 mmol), and cyclohexanecarbaldehyde (151 μl, 1.25 mmol) were mixed in DMF (10 ml). Sodium triacetoxyborohydride (390 mg, 1.84 mmol) was added to the above solution and the reaction mixture stirred at room temperature under N2 for 20 h. Additional cyclohexanecarbaldehyde (151 μl, 1.25 mmol) and sodium triacetoxyborohydride (390 mg, 1.84 mmol) were added and the reaction mixture was stirred 20 hours longer. The reaction was quenched with 0.33N NaOH (50 ml), and the product was extracted with DCM (50 ml). The DCM extract was dried (MgSO4), and the solvent was evaporated. The residue was purified by flash chromatography (DCM-MeOH, 95:5) to give the product as a beige solid (80 mg, 40% yield).

Workup

  1. stirringthe reaction mixture was stirred 20 hours longer
  2. customThe reaction was quenched with 0.33N NaOH (50 ml)
  3. extractionthe product was extracted with DCM (50 ml)
  4. extractionThe DCM extract
  5. dry with materialwas dried (MgSO4)
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography (DCM-MeOH, 95:5)

Sources & evidence

ORD record
ord-2e2a255fac514774842b1c94adcb4c93
Source dataset
uspto-grants-2007_10
Patent number
US07279575B2

Reaction notes

Loading…