Diisopropylethylamine → HCID 57744887, compound

HRID 1661494Notes

Reaction equation

HRID 1661494 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9]C)=O)=[C:4]([N:11]([CH3:20])[C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]=1[CH3:21].BrC1SC(C(OC)=O)=C(NC)C=1C.CCN(C(C)C)C(C)C.ClC(=O)CC(OCC)=O>CN(C)C1C=CN=CC=1.CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[S:6][C:5]2[C:7]([OH:9])=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12](=[O:19])[N:11]([CH3:20])[C:4]=2[C:3]=1[CH3:21]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 66743799HCID 66743799, compoundHCID 67429807HCID 67429807, compound

Product 1

HCID 57744887HCID 57744887, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-bromo-3-(3-ethoxy-N-methyl-3-oxopropanamido)-4-methylthiophene-2-carboxylate. A solution of methyl 5-bromo-4-methyl-3-(methylamino)thiophene-2-carboxylate (0.28 g, 1.1 mmol), DIEA (0.22 mL, 1.3 mmol), N,N-dimethylpyridin-4-amine (0.020 g, 0.16 mmol) in DMF (4 mL) was treated at room temperature with ethyl 3-chloro-3-oxopropanoate (0.16 mL, 1.3 mmol) and stirred for 18 hours. The mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4, and evaporated. The residue was purified by flash chromatography using EtOAc/hexanes to give the title compound. MS (ESI) m/z: Calculated 378.2; Observed; 379.0. 1H NMR (300 MHz, CDCl3) δ ppm 4.12-4.11 (2H, m), 3.86 (3H, s), 3.16 (3H, s), 3.12 (2H, s), 2.10 (3H, s), 1.23 (3H, t, J=7.1 Hz).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2f9dfcce218d4f2081c9ba8836f7e675
Source dataset
uspto-grants-2011_10
Patent number
US08030346B2

Reaction notes

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