Diisopropylethylamine → HCID 59312986, compound

HRID 2389751Notes

Reaction equation

HRID 2389751 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:3]=1.[NH2:19][CH:20]([CH3:30])[CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C(N(CC)C(C)C)(C)C>CS(C)=O.O.C(OCC)C>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:4]1[N:3]=[C:2]([NH:19][CH:20]([CH3:30])[CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 22499135tert-Butyl (2-aminopropyl)carbamateHCID 59312932HCID 59312932, compound

Product 1

HCID 59312986HCID 59312986, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

5-Chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine (Example 6A) (800 mg, 2.7 mmol), tert-butyl (2-aminopropyl)carbamate (700 mg, 4.0 mmol) and N,N-diisopropylethylamine (1.00 g, 8.0 mmol) are dissolved in DMSO (13 ml) and stirred at 120° C. under argon for 12 hours. The reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate (3×75 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. Removal of the solvent results in a foam which is taken up in diethyl ether. The product precipitates as solid from the diethyl ether solution and is filtered off with suction and dried. 800 mg (68% of theory) of the product are obtained as a solid.

Workup

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customRemoval of the solvent
  6. customresults in a foam which
  7. customThe product precipitates as solid from the diethyl ether solution
  8. filtrationis filtered off with suction
  9. customdried
  10. custom800 mg (68% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-cf53dc6daf8e417c94cf996c971758d8
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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