1,2-Dichloroethane → HCID 10291174, compound

HRID 1815178Notes

Reaction equation

HRID 1815178 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.CC[N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])C.C(Cl)CCl.C1C=C[C:33]2N(O)N=[N:36][C:34]=2C=1>C(Cl)Cl>[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:6]([C:2]2[S:1][CH:5]=[CH:4][C:3]=2[NH:36][CH2:34][C:33]2[CH:22]=[CH:20][N:19]=[CH:23][CH:25]=2)=[O:8])=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 78124-ChloroanilineHCID 107002-Thiophenecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 10291174HCID 10291174, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the thienyl carboxylic acid from Step A (300 mg, 1.23 mmol) and 4-chloroaniline (160 mg, 1.25 mmol) and DIEA (300 μl, 1.6 mmol) was added EDC (300 mg, 1.6 mmol) and HOBt (170 mg, 1.25 mmol) in CH2Cl2, the reaction was stirred at RT overnight. The solution was washed with 1N HCl and saturated NaHCO3, followed by H2O and brine. The organic layer was dried over Na2SO4 and evaporated under reduced pressure and purified with preparative TLC to give the amide. MS (ES+): 353 (M+H)+; (ES−): 351 (M−H)−.

Workup

  1. washThe solution was washed with 1N HCl and saturated NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated under reduced pressure
  4. custompurified with preparative TLC

Sources & evidence

ORD record
ord-e0295117f4af410dae795d4197d0225c
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

Loading…