Water → HCID 178457358, compound

HRID 511660Notes

Reaction equation

HRID 511660 reaction equation
FC(F)(F)C(O)=O.O.[C:9]([C:13]1[CH:63]=[CH:62][C:16]2[NH:17][C:18]([CH2:20][CH2:21][CH:22]3[CH2:25][CH:24]([N:26]([CH2:30][C@@H:31]4[C@H:35]5[O:36]C(C)(C)[O:38][C@H:34]5[C@H:33]([N:41]5[CH:49]=[N:48][C:47]6[C:42]5=[N:43][CH:44]=[N:45][C:46]=6[NH:50]CC5C=CC(OC)=CC=5OC)[CH2:32]4)[CH:27]([CH3:29])[CH3:28])[CH2:23]3)=[N:19][C:15]=2[CH:14]=1)([CH3:12])([CH3:11])[CH3:10].C([SiH](CC)CC)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[NH2:50][C:46]1[N:45]=[CH:44][N:43]=[C:42]2[C:47]=1[N:48]=[CH:49][N:41]2[C@@H:33]1[CH2:32][C@H:31]([CH2:30][N:26]([CH:24]2[CH2:25][CH:22]([CH2:21][CH2:20][C:18]3[NH:17][C:16]4[CH:62]=[CH:63][C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:14][C:15]=4[N:19]=3)[CH2:23]2)[CH:27]([CH3:28])[CH3:29])[C@@H:35]([OH:36])[C@H:34]1[OH:38]

Participants

8

Reactant 5

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 178491027HCID 178491027, compound

Product 1

HCID 178457358HCID 178457358, compoundYield 21.1%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

Trifluoroacetic Acid (10 ml, 100 mmol) added to a mixture of Water (1 ml, 60 mmol) and 9-((3aS,4R,6R,6aR)-6-(((3-(2-(5-(tert-butyl)-1H-benzo[d]imidazol-2-yl)ethyl)cyclobutyl)(isopropyl)amino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-N-(2,4-dimethoxybenzyl)-9H-purin-6-amine (0.91 g, 1.2 mmol) at RT. The reaction was stirred overnight at RT. The reaction was then heated to 35° C. and triethylsilane (0.39 ml, 2.4 mmol) was added. The reaction was stirred at 35° C. for a further 2 days. The volatiles were removed in vacuo and resulting residue was taken up in MeOH (15 mls). 500 mgs of K2CO3 and 8 drops H2O were added and reaction stirred at RT for 1 hour. The mixture was filtered and filter cake washed with 10 mls MeOH. The filtrate was concentrated and the resulting residue was purified by flash chromatography (DCM/7N NH3 in MeOH 90:10) to yield the desired product (0.142 g) as a colorless solid after several days of lyophilization.

Workup

  1. temperatureThe reaction was then heated to 35° C.
  2. stirringThe reaction was stirred at 35° C. for a further 2 days
  3. customThe volatiles were removed in vacuo
  4. customresulting residue
  5. customreaction
  6. stirringstirred at RT for 1 hour
  7. filtrationThe mixture was filtered
  8. filtrationfilter cake
  9. washwashed with 10 mls MeOH
  10. concentrationThe filtrate was concentrated
  11. customthe resulting residue was purified by flash chromatography (DCM/7N NH3 in MeOH 90:10)

Sources & evidence

ORD record
ord-2d394a021c0447de823e3b8d47c0518d
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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