Dimethylamine → HCID 178456091, compound

HRID 80580Notes

Reaction equation

HRID 80580 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([CH:33]=1)[CH2:7][C@H:8]1[C:14](=[O:15])[N:13]([C:16]([NH:18][C@H:19]([CH2:23][CH3:24])[C:20](O)=[O:21])=[O:17])[CH2:12][C:11](=[N:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:10][CH2:9]1.C(Cl)Cl.[CH3:39][NH:40]C.CO>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([CH:33]=1)[CH2:7][C@H:8]1[C:14](=[O:15])[N:13]([C:16]([NH:18][C@@H:19]([C:20](=[O:21])[NH:40][CH3:39])[CH2:23][CH3:24])=[O:17])[CH2:12][C:11](=[N:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:10][CH2:9]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 887MethanolHCID 6344DichloromethaneHCID 178456092HCID 178456092, compound

Product 1

HCID 178456091HCID 178456091, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To the compound 54 (70 mg) in a methylene chloride (3 ml) solution, dimethylamine in a methanol solution (2M, 0.14 ml), triethylamine (0.291 ml), and propyl phosphonate anhydride (T3P) (50% ethyl acetate solution, 0.21 ml) were successively added, and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off, and the residue was diluted with ethyl acetate. Then the resultant mixture was successively washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution, and brine. The organic layer was dried over anhydrous sodium sulfate, then was concentrated. The residue was purified by flash column chromatography (silica gel, chloroform/ethyl acetate=9/1 to 1/1) to obtain the title compound (42.5 mg).

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was diluted with ethyl acetate
  3. washThen the resultant mixture was successively washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationwas concentrated
  6. customThe residue was purified by flash column chromatography (silica gel, chloroform/ethyl acetate=9/1 to 1/1)

Sources & evidence

ORD record
ord-819ca6a525f64d84869671121d1edd81
Source dataset
uspto-grants-2014_09
Patent number
US08846660B2

Reaction notes

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