Methyl iodide → HCID 21905823, compound

HRID 1246825Notes

Reaction equation

HRID 1246825 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[N:24]2[CH2:37][CH2:36][C:27]3([N:31]([CH:32]([CH3:34])[CH3:33])[CH2:30][NH:29][C:28]3=[O:35])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1.[CH3:38]I.[H-].[Na+]>O1CCCC1.CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[N:24]2[CH2:37][CH2:36][C:27]3([N:31]([CH:32]([CH3:33])[CH3:34])[CH2:30][N:29]([CH3:38])[C:28]3=[O:35])[CH2:26][CH2:25]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10347100HCID 10347100, compound

Product 1

HCID 21905823HCID 21905823, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A suspension of 8-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-1-isopropyl-1,3,8-triazaspiro[4.5]decan-4-one 13A-1 (86 mg, 0.16 mmol) and methyl iodide (2 M in MTBE, 16 μl) in 1:1 tetrahydrofuran/dimethylformamide (2 ml) was treated with sodium hydride (60% dispersion in oil, 12 mg, 0.3 mmol). After stirring for 2 hours, the mixture was extracted from saturated aqueous sodium bicarbonate with ethyl acetate, dried (Na2SO4), concentrated (123 mg), and then purified by flash chromatography using 4% methanol to give title compound 25A-1 as an oil (87 mg, quantitative). A methylene chloride solution of the material was treated with excess 1 M HCl in ether, concentrated under a stream of nitrogen, and then triturated from ether to give the hydrochloride salt of compound 25A-1 (82 mg, 82% overall) as a colorless solid: +ESI MS (M+1) 550.2; 1H NMR (400 MHz, CD3OD) δ 8.34 (s, 1H), 7.60 (d, J=7.9 Hz, 1H), 7.51–7.39 (m, 5H), 7.31 (d, J=8.3 Hz, 2H), 4.76 (s, 2H), 4.14 (brs, 2H), 3.78 (brs, 1H), 2.96 (s, 3H), 2.28 (br s, 4H), 1.32 (d, J=6.2 Hz, 6H).

Workup

  1. extractionthe mixture was extracted from saturated aqueous sodium bicarbonate with ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated (123 mg)
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1c695e1ba9e64f4ba3c3ccebb8ebde05
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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