Methylamine → HCID 59513542, compound

HRID 1159860Notes

Reaction equation

HRID 1159860 reaction equation
I[CH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:3].[CH3:22][NH2:23]>C(Cl)Cl.CCO>[CH3:22][NH:23][CH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:3]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 68717446HCID 68717446, compound2×

Product 1

HCID 59513542HCID 59513542, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(1-iodoethyl)-1-(phenylsulfonyl)-1H-indole (50 mg, 122 μmol; Intermediate 99) in CH2Cl2 (1.5 mL) was treated with MeNH2 (153 μL of a 8 M solution in EtOH, 1.22 mmol) at rt for 2 h. The reaction mixture was concentrated in vacuo, the obtained residue taken up with MeOH/THF and purified by prep. HPLC (System B, 22-52% MeCN, 50 mM NH4HCO3) to yield the title compound as a white, waxy solid (13.2 mg, 12% over two steps). MS (ESI+) for C17H18N2O2S m/z 284 (M-NHMe)+, 315 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by prep

Sources & evidence

ORD record
ord-b2c7af42927742bfa3b884d038573afa
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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