Acetic Acid → HCID 59605361, compound

HRID 1945912Notes

Reaction equation

HRID 1945912 reaction equation
C([N:8]([CH2:45][CH2:46][O:47][CH3:48])[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)C1C=CC=CC=1.C(O)(=O)C>[Pd].C(O)C>[CH3:48][O:47][CH2:46][CH2:45][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

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59605724HCID 59605724, compound

Product 1

HCID 59605361HCID 59605361, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(1-((2-(2-(benzyl(methoxyethyl)amino)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol (0.22 g, 0.34 mmol) and palladium on carbon (10 wt %, 0.2 g) and acetic acid (0.15 mL) in ethanol (10 mL) was stirred under a hydrogen atmosphere at 70° C. for 18 hours. The reaction mixture was then filtered though celite and concentrated. The crude product was purified by RP-HPLC to give 358 (54 mg, 28%). LCMS m/z: 564.4 (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-2d08d3ef381742dbaf272be5b154939b
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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