Dimethylamine → HCID 67368575, compound

HRID 1753152Notes

Reaction equation

HRID 1753152 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][N:10]2[CH:14]=[C:13]([C:15](=[O:20])C(Cl)(Cl)Cl)[CH:12]=[C:11]2[C:21]([O:23][CH3:24])=[O:22])=[CH:4][CH:3]=1.[CH3:26][NH:27][CH3:28].[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][N:10]2[CH:14]=[C:13]([C:15](=[O:20])[N:27]([CH3:28])[CH3:26])[CH:12]=[C:11]2[C:21]([O:23][CH3:24])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 25517Ammonium ChlorideHCID 67367650HCID 67367650, compound

Product 1

HCID 67368575HCID 67368575, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-[2-(4-chlorophenyl)-2-oxoethyl]-4-(trichloroacetyl)-1H-pyrrole-2-carboxylate (97 mg, 0.23 mmol) in THF (2 mL) was added dimethylamine (50 μL, 0.75 mmol). The reaction mixture was stirred at room temperature. After completion (2.5 days, monitored by LCMS) a saturated aqueous solution of ammonium chloride (25 mL) was added and the mixture extracted with CH2Cl2 containing 20% of propan-2-ol (5×25 mL). The organic fractions were combined, dried (MgSO4) and concentrated in vacuo to give crude product mixture that was purified using flash chromatography (Biotage SP4, 12 g cartridge; 0-10% MeOH gradient in CH2Cl2) to give methyl 1-[2-(4-chlorophenyl)-2-oxoethyl]-4-(dimethylcarbamoyl)-1H-pyrrole-2-carboxylate (45 mg, yield 56%). 1H NMR (400 MHz, d6-acetone): δ 3.12 (br s, 6H), 3.70 (s, 3H), 5.97 (s, 2H), 7.19 (d, 1H, J 2.0 Hz), 7.48 (d, 1H, J 1.9 Hz), 7.62-7.66 (m, 2H), 8.08-8.13 (m, 2H).

Workup

  1. extractionthe mixture extracted with CH2Cl2 containing 20% of propan-2-ol (5×25 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give crude product mixture that
  5. customwas purified

Sources & evidence

ORD record
ord-3e39603d3ccc437e9017000bb30e3f85
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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