Tetrabutylammonium Fluoride → HCID 178461230, compound

HRID 1852879Notes

Reaction equation

HRID 1852879 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][O:29][C:30]1[C:35]([C:36]2[C:41]3[N:42]([CH2:54][C@H:55]4[CH2:60][CH2:59][C@H:58]([CH3:61])[CH2:57][CH2:56]4)[C:43]([N:45]4[CH2:50][CH2:49][O:48][C@@H:47]5[CH2:51][CH2:52][CH2:53][C@@H:46]45)=[N:44][C:40]=3[CH:39]=[C:38]([C:62]3[NH:66][C:65](=[O:67])[O:64][N:63]=3)[N:37]=2)=[CH:34][C:33]([Cl:68])=[CH:32][N:31]=1)(C(C)(C)C)(C)C>C1COCC1>[Cl:68][C:33]1[CH:34]=[C:35]([C:36]2[C:41]3[N:42]([CH2:54][C@H:55]4[CH2:60][CH2:59][C@H:58]([CH3:61])[CH2:57][CH2:56]4)[C:43]([N:45]4[CH2:50][CH2:49][O:48][C@@H:47]5[CH2:51][CH2:52][CH2:53][C@@H:46]45)=[N:44][C:40]=3[CH:39]=[C:38]([C:62]3[NH:66][C:65](=[O:67])[O:64][N:63]=3)[N:37]=2)[C:30]([O:29][CH2:28][CH2:27][OH:26])=[N:31][CH:32]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455297HCID 178455297, compound

Product 1

HCID 178461230HCID 178461230, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.1 mL, 1 M in THF, 0.1 mmol) was added to solution of 3-{4-[2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-5-chloropyridin-3-yl]-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (racemic, 20 mg, 0.027 mmol) in THF (1.0 mL) at room temperature and stirred for 16 hours. The reaction was concentrated, and the residue was dissolved in CH2Cl2/IPA (4:1, 15 mL) and washed twice using water (10 mL). The layers were separated, and the organic layer was concentrated under reduced pressure. Purification of the residue on a silica gel column with 0 to 10% MeOH/CH2Cl2 afforded 3-{4-[5-chloro-2-(2-hydroxyethoxy)pyridin-3-yl]-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (racemic). 1H NMR (400 MHz, CDCl3) δ 8.28 (br s, 2H), 7.26 (s, 1H), 4.70 (d, J=10.2 Hz, 1H), 3.90 (t, J=12.2 Hz, 2H), 3.70-3.80 (m, 3H), 3.45-3.74 (m, 2H), 3.17-3.32 (m, 2H), 3.10 (t, J=12.4 Hz, 2H), 2.39 (m, 1H), 1.99 (m, 1H), 1.88 (m, 1H), 1.66-1.76 (m, 2H), 1.45-1.62 (m, 6H), 1.02-1.32 (m, 2H), 0.88 (m, 1H), 0.77 (d, J=7.4 Hz, 3H), 0.42-0.60 (m, 2H). MS ES calc'd. for C30H36ClN7O5 [M−1]− 608. found 608.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2/IPA (4:1, 15 mL)
  3. washwashed twice using water (10 mL)
  4. customThe layers were separated
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customPurification of the residue on a silica gel column with 0 to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-f6858d3494534fd0a9d72fbad25ddd3b
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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