Diisopropylethylamine → HCID 21949932, compound

HRID 558281Notes

Reaction equation

HRID 558281 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[CH2:11][C:12]1[N:16]([CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[N:15]=[C:14]([CH2:27][CH3:28])[C:13]=1[O:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]2[N:16]([CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[N:15]=[C:14]([CH2:27][CH3:28])[C:13]=2[O:29][C:30]2[CH:31]=[C:32]([Cl:37])[CH:33]=[C:34]([Cl:36])[CH:35]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 837951-AcetylpiperazineHCID 21949785HCID 21949785, compound

Product 1

HCID 21949932HCID 21949932, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-Acetylpiperazine (42 mg, 0.330 mmol) in N,N-dimethylformamide (1 ml) was added to a stirred solution of the bromide of Example 137 (148 mg, 0.300 mmol) and diisopropylethylamine (57 μL, 0.330 mmol) in N,N-dimethylformamide (2 ml) at room temperature. The reaction was stirred for 5 hours and the mixture was concentrated under reduced pressure. A solution of the residue in dichloromethane (30 ml) was washed with 1M aqueous potassium carbonate solution (10 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume) to provide the title compound (150 mg) as a colourless oil.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. washA solution of the residue in dichloromethane (30 ml) was washed with 1M aqueous potassium carbonate solution (10 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume)

Sources & evidence

ORD record
ord-55fd915361454af3a7f51d4a121b3c68
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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