1,2-Dichloroethane → HCID 178520424, compound

HRID 1071996Notes

Reaction equation

HRID 1071996 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.Cl.[NH:34]1[C:42]2[CH2:41][CH2:40][NH:39][CH2:38][C:37]=2[N:36]=[CH:35]1>C(OCC)(=O)C.C(N(CC)CC)C>[C:12]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C:9]([N:39]2[CH2:40][CH2:41][C:42]3[NH:34][CH:35]=[N:36][C:37]=3[CH2:38]2)=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 64798Diphenylpropionic acidHCID 757711-HydroxybenzotriazoleHCID 164180044,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine--hydrogen chloride (1/2)

Product 1

HCID 178520424HCID 178520424, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 3,3-diphenylpropionic acid (14 mg, 0.06 mmol) and HOBt (9 mg, 0.07 mmol) in ethyl acetate (1.5 mL) a solution of EDC (12 mg, 0.06 mmol) in ethyl acetate (0.5 mL) was added. The resulting mixture was shaken for 20 min at room temperature and then 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (12 mg, 0.06 mmol) and triethylamine (0.02 mL) were added. After shaking for 16 h the mixture was washed with brine (2×2 mL), and the organic phase was concentrated. 12 mg (60%) of the title amide was obtained.

Workup

  1. additionwas added
  2. stirringAfter shaking for 16 h the mixture
  3. washwas washed with brine (2×2 mL)
  4. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-33573cc4d32b4795a0126561d29d21ae
Source dataset
uspto-grants-2005_06
Patent number
US06908926B1

Reaction notes

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