Triethylamine → HCID 59464692, compound

HRID 1046597Notes

Reaction equation

HRID 1046597 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH2:22])[C:12]2[N:13]=[C:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[S:15][CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31](O)=[O:32])[CH:27]=[CH:28][CH:29]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.O>[Cl:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([NH:22][C@H:11]([C:12]2[N:13]=[C:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[S:15][CH:16]=2)[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[O:32])[CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 158793-Chlorophenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 667053342-(4-Nitrophenyl)-1-(2-thiophene-2-ylthiazol-4-yl)ethylamine

Product 1

HCID 59464692HCID 59464692, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-nitropheyl)-1-(2-thiophene2-ylthiazol-4-yl)ethylamine, 22,(0.41 g, 1 mmol) 3-chlorophenylacetic acid (0.170 g, 1mmol) and 1-hydroxybenzotriazole (HOBt)(0.07 g, 0.05 mmol) in DMF (5 ml) at 0°, is added 1-(3-dimethylaminoprpyl)-3-ethylcarbodiimide (EDCI) (0.190 g, 1 mmol) followed by triethylamine (0.42 mL, 3 mmol). The mixture is stirred at 0° for 30 minutes then at room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combined organic phase is washed with 1 N aqueous HCI, 5% aqueoue NaHCO3, water and brine, and dried over Na2SO4. The solvent is removed in vacuo to afford 0.290 g (60% yield) of the desired product wich is used without further purification. SEI-MS 428 (M-1).

Workup

  1. customat room temperature
  2. customovernight
  3. extractionextracted with EtOAc
  4. washThe combined organic phase is washed with 1 N aqueous HCI, 5% aqueoue NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0473cb49042e4a1a85d8432869044ba5
Source dataset
uspto-grants-2013_10
Patent number
US08569348B2

Reaction notes

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