Acetic Acid → HCID 59605754, compound

HRID 1923008Notes

Reaction equation

HRID 1923008 reaction equation
[CH2:1]([N:8](CC)[C:9]1[N:13]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([C:31]([OH:34])([CH3:33])[CH3:32])[CH2:27][CH2:26]4)[N:20]3[CH3:23])=[C:16]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[N:15]=2)[C:12]2[CH:41]=[CH:42][CH:43]=[CH:44][C:11]=2[N:10]=1)[C:2]1C=CC=CC=1.C(O)(=O)C>[Pd].C(O)C>[CH2:1]([NH:8][C:9]1[N:13]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([CH2:24][N:25]4[CH2:26][CH2:27][CH:28]([C:31]([OH:34])([CH3:33])[CH3:32])[CH2:29][CH2:30]4)[N:20]3[CH3:23])=[C:16]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[N:15]=2)[C:12]2[CH:41]=[CH:42][CH:43]=[CH:44][C:11]=2[N:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59605969HCID 59605969, compound

Product 1

HCID 59605754HCID 59605754, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-(1-((2-(2-(benzyl(ethyl)amino)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol (0.6 mmol) and palladium on carbon (10 wt %, 0.3 g) and acetic acid (0.1 mL) in ethanol (20 mL) was stirred under a hydrogen atmosphere at 65° C. for 18 hours. The reaction mixture was then filtered though celite and concentrated. The crude product was purified by RP-HPLC to give 255 (28.5 mg, 17%). LCMS m/z: 534.3 (MH+)

Workup

  1. filtrationThe reaction mixture was then filtered though celite and
  2. concentrationconcentrated
  3. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-3dfbae80b341463a90b023cea4e82301
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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