Methyl iodide → HCID 57526532, compound

HRID 1453407Notes

Reaction equation

HRID 1453407 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:36]([O:38]C)=[O:37])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([C:21]([NH:23][CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[O:22])[CH2:18][C:17]4[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CI.[H-].[Na+].[CH3:44]NC(N)=O>CN(C=O)C.CO.CO.C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:36]([OH:38])=[O:37])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([C:21]([N:23]([CH3:44])[CH:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)=[O:22])[CH2:18][C:17]4[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 11719MethylureaHCID 24758Sodium hydrideHCID 57526670HCID 57526670, compound

Product 1

HCID 57526532HCID 57526532, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared from Methyl 13-cyclohexyl-3-(methyloxy)-6-((tetrahydro-2H-pyran-4-ylamino)carbonyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate by methylation using MeI and NaH in DMF in a similar manner as described before; Analytical thin layer chromatography (5% MeOH/CH2Cl2) Rf=0.30; Analytical HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Flow Rate=5 ml/min, Column: Xterra MS C18 S7 3.0×50 mm; LC/MS: (ES+) m/z (M+H)+=531.21, HPLC Rt=1.998 min.

Workup

  1. customB=100, Gradient time=2 min, Flow Rate=5 ml/min, Column

Sources & evidence

ORD record
ord-3a20b1a448d943de839af4c0b1077548
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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