Acetic Acid → HCID 49832107, compound

HRID 1945784Notes

Reaction equation

HRID 1945784 reaction equation
[CH2:1]([N:8](C)[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>[CH3:23][N:20]1[C:19]([CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([C:31]([OH:34])([CH3:33])[CH3:32])[CH2:27][CH2:26]2)=[N:18][C:17]2[C:21]1=[N:22][C:14]([N:13]1[C:12]3[CH:41]=[CH:42][CH:43]=[CH:44][C:11]=3[N:10]=[C:9]1[NH:8][CH3:1])=[N:15][C:16]=2[N:35]1[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 49832106HCID 49832106, compound

Product 1

HCID 49832107HCID 49832107, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(1-((2-(2-(benzyl(methyl)amino)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol 205 (0.2 g, 0.33 mmol) and palladium on carbon (10 wt %, 0.1 g) and acetic acid (0.1 mL) in ethanol (10 mL) was stirred under a hydrogen atmosphere at 60 degrees for 18 hours. The reaction mixture was then filtered though celite and concentrated. The crude product was purified by RP-HPLC to give 206 (28.5 mg, 17%). LCMS m/z: 520.3 (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-fe29966679cf4436aaf0e3403f19271f
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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