Triethylamine → HCID 178483824, compound

HRID 1611401Notes

Reaction equation

HRID 1611401 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13](Cl)=[O:14])=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[OH:22].[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27].C(N(CC)CC)C>ClCCl>[NH3:10].[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH:27][C:13]([C:11]1[NH:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([OH:22])[CH:4]=2)=[C:9]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:10]=1)=[O:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 178521130HCID 178521130, compound

Product 2

HCID 222AmmoniaHCID 178483824HCID 178483824, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product from Step 2 (124 mg, 0.3 mmol) was suspended in dichioromethane (5 ml) and treated with a solution of N,N-dimethyl ethylenediamine (0.036 ml, 0.33 mmol), and triethylamine (0.125 ml, 0.9 mmol) in dichloromethane (1 ml). The reaction mixture was then stirred at room temperature overnight, washed saturated sodium bicarbonate solution (3 ml) and passed through a Varain Chem Elut hydromatric cartridge to remove the aqueous phase. The filtrate was then concentrated and purified by silica gel chromatography, eluting with 0.3:3:7 dichloromethane: ethanol:0.880 ammonia solution to afford the title compound (20 mg, 17%); MS(AP+) m/e 386/388 [M+H]+

Workup

  1. washwashed saturated sodium bicarbonate solution (3 ml)
  2. customto remove the aqueous phase
  3. concentrationThe filtrate was then concentrated
  4. custompurified by silica gel chromatography
  5. washeluting with 0.3:3:7 dichloromethane

Sources & evidence

ORD record
ord-1b3b15d0610145598a11aecad3346288
Source dataset
uspto-grants-2006_01
Patent number
US06987119B2

Reaction notes

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