Acetone → HCID 178456241, compound

HRID 243302Notes

Reaction equation

HRID 243302 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH:18][C:19]2[N:27]=[CH:26][N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][NH:23]3)[CH3:17])[CH2:2]1.[CH3:28][C:29]([CH3:31])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.CC(O)=O>[CH:29]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH:18][C:19]2[N:27]=[CH:26][N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][NH:23]3)[CH3:17])[CH2:2]1)([CH3:31])[CH3:28]

Participants

7

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 178461909HCID 178461909, compound

Product 1

HCID 178456241HCID 178456241, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of [(S)-1-((R)-1-piperidin-3-yl-1H-benzoimidazol-2-yl)ethyl]-(9H-purin-6-yl)amine from Example 16 (150 mg, 0.414 mmol) in anhydrous DCM (3 mL) was added acetone (90 μL, 1.24 mmol) followed by AcOH (1 drop). After stirring for 5 min, sodium triacetoxyborohydride (132 mg, 0.621 mmol) was added and stirring was continued for 22 h. The mixture was then treated with NaOH (1N, 2 mL) and then vigorously stirred for 10 min. Volatiles were removed in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-15% 2M NH3/MeOH in DCM) affording 132 (58 mg, 35%). LCMS: RT 1.91 min [M+H]+ 405.1. 1H NMR (DMSO, 400 MHz): δ 12.97 (1H, s), 8.33-8.06 (2H, m), 7.96 (1H, br), 7.72 (1H, d, J=7.33 Hz), 7.62 (1H, d, J=7.14 Hz), 7.24-7.07 (2H, m), 5.93 (1H, s), 4.66-4.52 (1H, m), 3.00-2.83 (2H, m), 2.81-2.65 (2H, m), 2.23 (1H, t, J=11.59 Hz), 2.15-2.01 (1H, m), 1.84-1.57 (5H, m), 1.26-1.07 (1H, m), 0.96 (6H, d, J=6.51 Hz)

Workup

  1. stirringstirring
  2. waitwas continued for 22 h
  3. stirringvigorously stirred for 10 min
  4. customVolatiles were removed in vacuo
  5. customthe resulting residue was purified by column chromatography (Si—PCC, gradient 0-15% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-1f796096782446ba9dede8d8bbc68636
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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