Diisopropylethylamine → HCID 10480672, compound

HRID 2118057Notes

Reaction equation

HRID 2118057 reaction equation
C([N:4](CC)C(C)C)(C)C.[CH3:10][N:11]([CH3:16])[S:12](Cl)(=[O:14])=[O:13].[Cl:17][C:18]1[CH:43]=[CH:42][C:21]2[N:22]3[C:26]([CH2:27][NH:28][CH2:29][C:20]=2[CH:19]=1)=[N:25][N:24]=[C:23]3[CH:30]1[CH2:35][CH2:34][N:33]([C:36]2[N:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[CH2:32][CH2:31]1>ClCCl>[NH3:4].[CH3:10][N:11]([CH3:16])[S:12]([N:28]1[CH2:27][C:26]2[N:22]([C:23]([CH:30]3[CH2:31][CH2:32][N:33]([C:36]4[N:37]=[CH:38][CH:39]=[CH:40][N:41]=4)[CH2:34][CH2:35]3)=[N:24][N:25]=2)[C:21]2[CH:42]=[CH:43][C:18]([Cl:17])=[CH:19][C:20]=2[CH2:29]1)(=[O:14])=[O:13]

Participants

6

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 83372Dimethylsulphamoyl chloride2×HCID 21925629HCID 21925629, compound

Product 2

HCID 222AmmoniaHCID 10480672HCID 10480672, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (77 μl, 0.44 mmol), followed by dimethylsulphamoyl chloride (50 μl, 0.44 mmol) were added to an ice-cold solution of the amine from example 12 (150 mg, 0.4 mmol) in dichloromethane (10 ml), and the reaction mixture was stirred at room temperature for 4 hours. TLC analysis showed that starting material remained, so additional dimethylsulphamoyl chloride (91 μl, 0.8 mmol) and N,N-diisopropylethylamine (140 μl, 0.8 mmol) were added, and the mixture was stirred at room temperature for a further 18 hours. The mixture was evaporated under reduced pressure, the residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution, the layers were separated, and the organic phase was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant, to afford the title compound as an off-white solid (135 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for a further 18 hours
  2. customThe mixture was evaporated under reduced pressure
  3. customthe residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution
  4. customthe layers were separated
  5. customthe organic phase was evaporated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-151eacdd1f9d4134a7acec9805dd418c
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

Loading…