Diisopropylethylamine → HCID 21925634, compound

HRID 2118051Notes

Reaction equation

HRID 2118051 reaction equation
C([N:4](CC)C(C)C)(C)C.Br[CH2:11][O:12][CH2:13][CH3:14].[Cl:15][C:16]1[CH:41]=[CH:40][C:19]2[N:20]3[C:24]([CH2:25][NH:26][CH2:27][C:18]=2[CH:17]=1)=[N:23][N:22]=[C:21]3[CH:28]1[CH2:33][CH2:32][N:31]([C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:30][CH2:29]1>CN(C)C=O>[NH3:4].[Cl:15][C:16]1[CH:41]=[CH:40][C:19]2[N:20]3[C:24]([CH2:25][N:26]([CH2:14][CH2:13][O:12][CH3:11])[CH2:27][C:18]=2[CH:17]=1)=[N:23][N:22]=[C:21]3[CH:28]1[CH2:33][CH2:32][N:31]([C:34]2[N:35]=[CH:36][CH:37]=[CH:38][N:39]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 111054342-bromomethoxyethaneHCID 21925629HCID 21925629, compound

Product 2

HCID 222AmmoniaHCID 21925634HCID 21925634, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N,N-Diisopropylethylamine (80 μl, 0.62 mmol), followed by 2-bromomethoxyethane (0.2 ml, 0.62 mmol) were added to a solution of the amine from example 12 (200 mg, 0.52 mmol) in N,N-dimethylformamide (6 ml) and the reaction mixture was stirred at 80° C. for 18 hours. The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica gel using ethyl acetate:methanol:0.88 ammonia (95:5:0.5) to give the title compound as a gum (76 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-124761ca46824c47ac7890ea1b38a862
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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