Triethylamine → HCID 178473532, compound

HRID 1428814Notes

Reaction equation

HRID 1428814 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]=S.C(N(CC)CC)C.[NH:27]1[CH:31]=[C:30]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:29]=[N:28]1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:35]([O:34][C:32]([C:30]1[CH:31]=[N:27][N:28]([C:13]([NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:12][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:29]=1)=[O:33])[CH3:36]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 227703,4-DimethoxyanilineHCID 85320Ethyl isothiocyanatoformateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 178473532HCID 178473532, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,4-dimethoxyaniline (0.15 g, 1.0 mmol), ethyl isothiocyanatoformate (0.14 mL, 1.2 mmol) and DCM (10 mL) was stirred at room temperature for 1 h. Triethylamine (0.42 mL, 3.0 mmol), ethyl pyrazole-4-carboxylate (0.17 g, 1.2 mmol), and EDCl (0.19 g, 1.2 mmol) were added and the solution was stirred at room temperature for 5 h. The mixture was concentrated, diluted with water, and extracted with DCM. The organic layer was dried and concentrated to provide the crude titled compound (390 mg, 100%). This material was used without purification: MS (ESI): mass calcd. for C18H22N4O6, 390.4; m/z found, 391.4 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db46dc49439f48828359408429ab7a7a
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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