1,2-Dichloroethane → HCID 69936757, compound

HRID 1623780Notes

Reaction equation

HRID 1623780 reaction equation
[CH:1]1[CH:2]=C[C:4]2[N:9](O)N=[N:7][C:5]=2[CH:6]=1.[CH3:11][N:12]([CH3:32])[C:13]([C:15]1[CH:16]=[CH:17][C:18]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:19]([CH:23]=1)[C:20]([OH:22])=O)=[O:14].N1C=CC=C(N)C=1.C(Cl)CCl>CN(C)C=O.O>[CH3:32][N:12]([CH3:11])[C:13]([C:15]1[CH:16]=[CH:17][C:18]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:19]([C:20]([NH:7][C:5]2[CH:4]=[N:9][CH:2]=[CH:1][CH:6]=2)=[O:22])[CH:23]=1)=[O:14]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 67106993HCID 67106993, compound

Product 1

HCID 69936757HCID 69936757, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HOBT (102 mg, 0.67 mmol) was added in one charge to a stirred solution of 5-[(dimethylamino)carbonyl]-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 59; 200 mg, 0.67 mmol), 3-pyridinamine (62.9 mg, 0.67 mmol) and EDC (128 mg, 0.67 mmol) in N,N-dimethylformamide (5 ml) under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 4 h. The mixture was diluted with water (50 ml). The precipitate was collected by filtration. The solid was dissolved in ethyl acetate (100 ml), and the organic phase was washed with NaOH (1 mol/l 25 ml), water (25 ml), saturated brine (25 ml), dried over sodium sulfate, and evaporated in vacuo to yield the title compound as a white solid. 78 mg.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutionThe solid was dissolved in ethyl acetate (100 ml)
  3. washthe organic phase was washed with NaOH (1 mol/l 25 ml), water (25 ml), saturated brine (25 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9d148bd02f994cab8908feea5236dd69
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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