Methyl iodide → HCID 178484790, compound

HRID 1711795Notes

Reaction equation

HRID 1711795 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]4[N:20]([C:22]([C@H:25]5[CH2:30][CH2:29][C@H:28]([NH:31][C:32](=O)OC(C)(C)C)[CH2:27][CH2:26]5)=[N:23][N:24]=4)[CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.CI.[H-].[Na+].C(O)(C(F)(F)F)=O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]4[N:20]([C:22]([C@H:25]5[CH2:30][CH2:29][C@H:28]([NH:31][CH3:32])[CH2:27][CH2:26]5)=[N:23][N:24]=4)[CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 24758Sodium hydrideHCID 178453875HCID 178453875, compound

Product 1

HCID 178484790HCID 178484790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 mL round-bottom flask was added tert-butyl (trans)-4-(6-(6-(4-fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)cyclohexylcarbamate (4.00 g, 7.74 mmol; Example # K.1.1.35) and MeI (0.533 mL, 8.52 mmol) which were then dissolved in THF (10 mL). NaH (0.619 g, 15.5 mmol) was added. The reaction was allowed to stir for about 16 h at ambient temperature after which time TFA (5 mL) was added. The reaction was allowed to stir at ambient temperature for about 2 h after which time the reaction was quenched with aqueous NaHCO3 and the organic layer was separated. The aqueous layer was washed with DCM and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using EtOAc/MeOH (gradient, 1:0 to 9:1) to provide the title compound. (0.032 g, 1.0%): LC/MS (Table 1, Method a) Rt, =1.6 min; MS m/z: 431.2 (M+H)+.

Workup

  1. additionwas added
  2. customwas quenched with aqueous NaHCO3
  3. customthe organic layer was separated
  4. washThe aqueous layer was washed with DCM
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8ac6b0a34af14860bae7af69254023bc
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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