1,2-Dichloroethane → HCID 53740309, compound

HRID 2251926Notes

Reaction equation

HRID 2251926 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([OH:11])=O)[CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:26]1([C@@H:32]2[CH2:34][C@H:33]2[C:35]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][NH2:42])=[O:36])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[C:26]1([C@@H:32]2[CH2:34][C@H:33]2[C:35]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:9](=[O:11])[CH:8]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:36])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 54320763HCID 54320763, compound

Product 1

HCID 53740309HCID 53740309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.4 g (16.1 mmol) 3-(3-pyridyl)-acrylic acid and 5.3 ml (38.0 mmol) TEA are suspended in 80 ml abs. dichloromethane and cooled to ca. 0° C. under moisture exclusion. 2.9 g (18.9 mmol) 88% HOBT and 3.6 g (18.8 mmol) EDC are added and the mixture is stirred for 30 min under ice cooling. 5.3 g (17.0 mmol) 4-(trans-2-phenyl-cyclopropyl-carbonylamino)-butylamine are dissolved in 30 ml abs. dichloromethane and added drop-wise under ice cooling. The mixture is stirred overnight at RT without further cooling. The formed precipitate is filtered off and crystallized from 120 ml isopropanol. Colorless crystals with MP. 194-196° C. Yield 4.2 g (71%).

Workup

  1. stirringThe mixture is stirred overnight at RT without further cooling
  2. filtrationThe formed precipitate is filtered off
  3. customcrystallized from 120 ml isopropanol
  4. customwith MP. 194-196° C

Sources & evidence

ORD record
ord-c1a0244f2c7e41bd97f433f5d4970ebf
Source dataset
uspto-grants-2008_01
Patent number
US07320993B1

Reaction notes

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