Methyl iodide → HCID 68519081, compound

HRID 1992406Notes

Reaction equation

HRID 1992406 reaction equation
[C:1]([C:3]1[CH:33]=[CH:32][C:6]([O:7][CH2:8][CH2:9][N:10]2[CH2:17][CH:16]3[O:18][CH:12]([CH2:13][N:14]([CH2:19][CH2:20][NH:21][S:22]([C:25]4[C:26]([CH3:31])=[N:27][O:28][C:29]=4[CH3:30])(=[O:24])=[O:23])[CH2:15]3)[CH2:11]2)=[CH:5][CH:4]=1)#[N:2].[C:34]([O-])([O-])=O.[Cs+].[Cs+].IC>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][N:10]2[CH2:17][CH:16]3[O:18][CH:12]([CH2:13][N:14]([CH2:19][CH2:20][N:21]([CH3:34])[S:22]([C:25]4[C:26]([CH3:31])=[N:27][O:28][C:29]=4[CH3:30])(=[O:24])=[O:23])[CH2:15]3)[CH2:11]2)=[CH:32][CH:33]=1)#[N:2]

Participants

4

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 11591010HCID 11591010, compound

Product 1

HCID 68519081HCID 68519081, compoundYield 88.5%

Procedure

N-(2-{7-[2-(4-cyanophenoxy)ethyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}ethyl)-3,5-dimethylisoxazole-4-sulfonamide (43 mg, 0.09 mmol, from example 9 above ) and Cs2CO3 (86 mg, 0.26 mmol) were suspended in acetouitrile (2 mL). Iodomethane (17 μl , 0.26 mmol) was added and the reaction mixture was stirred at room temperature overnight under a nitrogen amosphere. More iodomethane (17 μl, 0.26 mmol) was added. The reaction mixture was left to stir for a further 20 h at room temperature overnight under a nitrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 39 mg (88%) of the title compound.

Workup

  1. waitThe reaction mixture was left
  2. stirringto stir for a further 20 h at room temperature overnight under a nitrogen atmosphere
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-48ee49f881e44d8d81ddd8a0b210073a
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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