Methyl iodide → HCID 66634917, compound

HRID 510070Notes

Reaction equation

HRID 510070 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:4]=1[CH2:5][N:6]1[C:10]2[N:11]=[C:12]([C:15]3[C:23]4[C:18](=[N:19][CH:20]=[C:21]([F:24])[CH:22]=4)[N:17]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[F:32])[N:16]=3)[N:13]=[CH:14][C:9]=2[NH:8][S:7]1(=[O:34])=[O:33].[C:41](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:4]=1[CH2:5][N:6]1[C:10]2[N:11]=[C:12]([C:15]3[C:23]4[C:18](=[N:19][CH:20]=[C:21]([F:24])[CH:22]=4)[N:17]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[F:32])[N:16]=3)[N:13]=[CH:14][C:9]=2[N:8]([CH3:41])[S:7]1(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 66635554HCID 66635554, compound

Product 1

HCID 66634917HCID 66634917, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

130 mg (approx. 0.115 mmol, 50% purity) of the compound from example 99A were initially charged in 5 ml of DMF, 44 mg (0.138 mmol) of cesium carbonate and 8.5 μl (0.138 mmol) of iodomethane were added and the mixture was stirred at RT overnight. Subsequently, another 14.3 μl (0.230 mmol) of iodomethane were added and the mixture was heated to 50° C. overnight. After cooling, the mixture was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). This gave 30.9 mg (46% of theory) of the title compound.

Workup

  1. temperaturethe mixture was heated to 50° C. overnight
  2. temperatureAfter cooling
  3. customthe mixture was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-ad5d4a5401fd4246bd0f4ec9c0a6c92b
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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