Methyl iodide → HCID 59857524, compound

HRID 555424Notes

Reaction equation

HRID 555424 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][C:8]2[NH:9][C:10]([NH:12][C:13]3[C:14]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:15][CH:16]=[CH:17][CH:18]=3)=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:35]>C1COCC1>[C:1]([C:5]1[CH:31]=[CH:30][C:8]2[N:9]=[C:10]([NH:12][C:13]3[C:14]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:15][CH:16]=[CH:17][CH:18]=3)[N:11]([CH3:35])[C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178440697HCID 178440697, compound

Product 1

HCID 59857524HCID 59857524, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-tert-Butyl-N-(2-(2-tert-butylphenoxy)pyridine-3-yl)-1H-benzo[d]imidazol-2-amine (Example 6, 50 mg, 0.121 mmol) was dissolved in THF (2 mL). At 0° C., NaH (2.6 mg, 0.109 mmol) was added and the mixture stirred for 11 min. ICH3 (15 mg, 0.109 mmol) was then slowly introduced. The solution turned purple. After 15 min additional stirring, the solvent was removed under vacuum and the crude product was purified by column chromatography on silica gel (eluting with a continuous gradient of MeOH from 0% to 5% in CH2Cl2). tR=6.265 min (Shimadzu Phenomenex S5 ODS 4.6×50 mm Luna 4.6×50 mm; flow rate 2.5 mL/mn; detection at 220 nM; Gradient elution 0% to 100% B over 8 min; (A=10% MeOH, 90% H2O, 0.2% H3PO4 & B=90% MeOH, 10% H2O, 0.2% H3PO4). HRMS (ESI) m/z calcd for C27H32N4O [M+H]+ 429.2654. found 429.2636.

Workup

  1. waitAfter 15 min additional stirring
  2. customthe solvent was removed under vacuum
  3. customthe crude product was purified by column chromatography on silica gel (
  4. washeluting with a continuous gradient of MeOH from 0% to 5% in CH2Cl2)
  5. washGradient elution 0% to 100% B over 8 min

Sources & evidence

ORD record
ord-8725dd6327234870a8955b6f329c0fe9
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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