Ethylamine hydrochloride → HCID 20815578, compound

HRID 747527Notes

Reaction equation

HRID 747527 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[N:13]([CH2:14][CH2:15][CH2:16][NH:17][CH2:18][C:19]([OH:21])=O)[C:12]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)=[CH:11][S:10]2)=[CH:4][CH:3]=1.Cl.[CH2:35]([NH2:37])[CH3:36].C(N(C(C)C)CC)(C)C.N=C=N>ClCCl.CN(C)C=O>[CH2:35]([NH:37][C:19](=[O:21])[CH2:18][NH:17][CH2:16][CH2:15][CH2:14][N:13]1[C:12]([C:22]2[CH:23]=[CH:24][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:26][CH:27]=2)=[CH:11][S:10][C:9]1=[N:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH3:36]

Participants

7

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 160435CarbodiimideHCID 22350973HCID 22350973, compound

Product 1

HCID 20815578HCID 20815578, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

The title compound was synthesized by combinatorial chemistry technique. That is, to a solution of the compound obtained in Example 329 (2) in dichloromethane (43.8 μmol/ml) (1 ml) were added a solution of ethylamine hydrochloride in N,N-dimethylformamide (35.0 μmol/ml) (1 ml), a solution of diisopropylethylamine (35.0 μmol/ml) (1 ml) and a suspension of carbodiimide resin in dichloromethane (79.2 mg/ml, manufactured by Argonaut) (1 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was filtered, and the filter cake was washed twice with dichloromethane (1 ml), and the filtrate was washed with a saturated aqueous sodium hydrogen carbonate solution (2 ml), and then washed twice with water (2 ml). The organic layer was passed through a filter containing magnesium sulfate, and the filter was washed twice with dichloromethane (1 ml), and the filtrate was concentrated. To the residue was added a 90% trifluoroacetic acid (2 ml), and the mixture was stirred at room temperature for 2 hours, and concentrated. The residue was dissolved in dichloromethane (2 ml), and excess amount of ion-exchange resin (Dowex 1-X8, OH-type) was added thereto, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filter cake was washed twice with dichloromethane (1 ml), and the filtrate was concentrated to give the title compound (6 mg).

Workup

  1. customThe title compound was synthesized by combinatorial chemistry technique
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was washed twice with dichloromethane (1 ml)
  4. washthe filtrate was washed with a saturated aqueous sodium hydrogen carbonate solution (2 ml)
  5. washwashed twice with water (2 ml)
  6. additioncontaining magnesium sulfate
  7. washthe filter was washed twice with dichloromethane (1 ml)
  8. concentrationthe filtrate was concentrated
  9. additionTo the residue was added a 90% trifluoroacetic acid (2 ml)
  10. stirringthe mixture was stirred at room temperature for 2 hours
  11. concentrationconcentrated
  12. dissolutionThe residue was dissolved in dichloromethane (2 ml)
  13. additionexcess amount of ion-exchange resin (Dowex 1-X8, OH-type) was added
  14. stirringthe mixture was stirred at room temperature for 1 hour
  15. filtrationThe reaction mixture was filtered
  16. washthe filter cake was washed twice with dichloromethane (1 ml)
  17. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-42145c90a07a4b20b3dee17ea7ce278a
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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