HCID 57527283, compound → HCID 58762309, compound

HRID 1453249Notes

Reaction equation

HRID 1453249 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:15][C:16]2([CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[O:21][C:20](=[O:22])[C:19]([CH2:23][C:24]3[N:34]=[C:27]4[N:28]=[C:29]([CH3:33])[CH:30]=[C:31]([CH3:32])[N:26]4[N:25]=3)=[C:18]([OH:35])[CH2:17]2)[CH:5]=[CH:6][C:7]=1[C:8]1([CH3:13])OCC[O:9]1>CC(C)=O>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([CH2:14][CH2:15][C:16]2([CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[O:21][C:20](=[O:22])[C:19]([CH2:23][C:24]3[N:34]=[C:27]4[N:28]=[C:29]([CH3:33])[CH:30]=[C:31]([CH3:32])[N:26]4[N:25]=3)=[C:18]([OH:35])[CH2:17]2)=[CH:3][C:2]=1[Cl:1])(=[O:9])[CH3:13]

Participants

3

Reactant 1

HCID 57527283HCID 57527283, compound

Product 1

HCID 58762309HCID 58762309, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The title compound was prepared in the following way: Example B(122) 6-{2-[3-Chloro-4-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-ethyl}-6-cyclopentyl-3-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-4-hydroxy-5,6-dihydro-pyran-2-one (0.138 g, 0.24 mmol), was dissolved in acetone (8 mL). Amberlyst-13 (0.23 g) was added from top and reaction was stirred under nitrogen for 72 hours at room temperature. The resulting reaction mixture was filtered through fritted funnel to remove the amberlyst and the resultant filtrate was diluted with EtOAC and washed with water (10 mL) and brine (10 mL) then dried over Na2SO4, filtered and concentrated. The resultant solid was recrystallized from MeOH to yield the product as a white solid (0.05 g, 41%). 1H NMR (400 MHz, DMSO-d6): δ 1.5-1.7 (m, 9H) 2.20-2.22 (m, 2H), 2.49-2.90 (m, 10H), 3.39 (s, 3H), 3.78 (d, J=16 Hz, 1H), 3.90 (d, J=16 Hz, 1H), 7.13 (s, 1H), 7.32 (s, 1H), 7.36 (d, J=8 Hz, 1H), 7.61 (d, J=8 Hz, 1H), 10.9 (s, 1H). MS (ESI): 523 (M+H)+.

Workup

  1. additionAmberlyst-13 (0.23 g) was added from top and reaction
  2. customThe resulting reaction mixture
  3. filtrationwas filtered through fritted funnel
  4. customto remove the amberlyst
  5. additionthe resultant filtrate was diluted with EtOAC
  6. washwashed with water (10 mL) and brine (10 mL)
  7. dry with materialthen dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resultant solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-151caf4565c8429db45a7ecb39a83b79
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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