Acetic Acid → HCID 59605791, compound

HRID 1946028Notes

Reaction equation

HRID 1946028 reaction equation
C([N:8](CC1C=CC=CC=1)[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>C(O)C.[Pd]>[NH2:8][C:9]1[N:13]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([CH2:24][N:25]4[CH2:30][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[CH2:36][CH2:37][O:38][CH2:39][CH2:40]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 59605369HCID 59605369, compound

Product 1

HCID 59605791HCID 59605791, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a flask of 2-(1-((2-(2-(dibenzylamino)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol (125 mg) in Ethanol (5.4 mL) was added 10% Palladium on Carbon (0.2 g) and Acetic acid (83 uL). The flask was purged with a nitrogen balloon and then placed under a Hydrogen balloon. The reaction was heated at 70° C. for 48 hours. The reaction was filtered thru celite and the celite cake was rinsed with a mixture of 1% acetic acid in methanol several times. The solvent was concentrated to dryness to give 70 mg of crude 2-(1-((2-(2-amino-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol, 70 mg of which was added to HATU (105 mg), DIPEA (0.12 mL) and acetic acid (24 uL) in DMF (0.8 mL). Upon completion, the reaction was diluted with Ethyl acetate and extracted with water. The organic layer was dried, filtered and concentrated to give crude product. The crude was purified via reverse phase HPLC to afford 11.5 mg of 517 as a white solid. MS (Q1) 548.3 (M)+

Workup

  1. customThe flask was purged with a nitrogen balloon
  2. filtrationThe reaction was filtered thru celite
  3. washthe celite cake was rinsed with a mixture of 1% acetic acid in methanol several times
  4. concentrationThe solvent was concentrated to dryness

Sources & evidence

ORD record
ord-67741836404348de96d124854347f09d
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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