Diisopropylethylamine → HCID 20607320, compound

HRID 431021Notes

Reaction equation

HRID 431021 reaction equation
C(N(C(C)C)CC)(C)C.[Br:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([O:28][CH2:29][CH2:30]Br)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:14]=[CH:15][CH:16]=1.[OH:34][C@@H:35]([CH3:46])[CH2:36][NH:37][CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>C(#N)C>[Br:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([O:28][CH2:29][CH2:30][N:37]([CH2:38][C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[CH2:36][C@@H:35]([OH:34])[CH3:46])[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15908942HCID 15908942, compoundHCID 18762828HCID 18762828, compound

Product 1

HCID 20607320HCID 20607320, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

0.25 ml of diisopropylethylamine are added to 650 mg of 4-[(3-bromo-phenyl)amino]-6-(2-bromoethoxy)-7-methoxy-quinazoline and 1.10 g of tert.butyl (S)-(2-hydroxy-propylamino)-acetate in 15 ml of acetonitrile. The reaction mixture is stirred overnight at 50° C. Since no reaction can be detected, the reaction mixture is concentrated by evaporation, combined with 20 ml of N,N-dimethylformamide and stirred for eight hours at 60° C. Then the temperature is increased to 80° C. After another eight hours the reaction is complete. The reaction mixture is concentrated by evaporation and chromatographed over a silica gel column with ethyl acetate as eluant. The desired product is obtained as a white solid.

Workup

  1. customSince no reaction
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. stirringstirred for eight hours at 60° C
  4. temperatureThen the temperature is increased to 80° C
  5. waitAfter another eight hours the reaction is complete
  6. concentrationThe reaction mixture is concentrated by evaporation
  7. customchromatographed over a silica gel column with ethyl acetate as eluant

Sources & evidence

ORD record
ord-21234a1e60534b1291c839a5c9319718
Source dataset
uspto-grants-2003_12
Patent number
US06656946B2

Reaction notes

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