Triethylamine → HCID 59587584, compound

HRID 714936Notes

Reaction equation

HRID 714936 reaction equation
Cl.[NH2:2][CH:3]([C:9](=[O:15])[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].O.OC1C2N=NNC=2C=CC=1.[F:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:29]=1[C:30](O)=[O:31].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[F:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:29]=1[C:30]([NH:2][CH:3]([C:9](=[O:15])[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:31]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 97962,6-Difluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68518842HCID 68518842, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 59587584HCID 59587584, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of crude ethyl 2-amino-3-oxo-3-(thiophen-2-yl)propanoate hydrochloride (0.44 g), hydroxybenzotriazole monohydrate (0.417 g, 2.7 mmol) and 2,6-difluorobenzoic acid (0.431 g, 2.7 mmol) in DMF (5.5 mL) was added triethylamine (0.38 mL, 5.2 mmol) followed by 1-(3-(dimethylamino)propyl)-3-ethyl-carbodiimide hydrochloride (0.575 g, 3.0 mmol). The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was partitioned between water and DCM. The organic phase was separated, washed with water, dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel column chromatography using 20% EtOAc in hexane as eluant to afford ethyl 2-(2,6-difluorobenzamido)-3-oxo-3-(thiophen-2-yl)propanoate (0.123 g, 0.35 mmol, 20%). 1H NMR (CDCl3) 1.27 (3H, t), 4.28 (2H, m), 6.21 (1H, d), 7.00 (2H, t), 7.26 (1H, dd), 7.44 (2H, m), 7.83 (1H, dd), 8.20 (1H, dd). LCMS (1) Rt: 2.10 min; m/z (ES+) 354.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water and DCM
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a786424a518a41a0ba87383f80b128c0
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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