1,2-Dichloroethane → HCID 67107360, compound

HRID 1623798Notes

Reaction equation

HRID 1623798 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[C:13]([CH:17]=1)[C:14](O)=[O:15].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C)C=O.O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[C:13]([CH:17]=1)[C:14]([NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:15]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 8706995HCID 8706995, compound

Product 1

HCID 67107360HCID 67107360, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Neat pyridin-3-amine (116 mg, 1.23 mmol) was added in one charge to a stirred suspension of 5-bromo-2-{[(3-fluorophenyl)methyl]oxy}benzoic acid (may be prepared as described in Description 83; 200 mg, 0.62 mmol), EDC (354 mg, 1.85 mmol), HOBT (283 mg, 1.85 mmol) and triethylamine (0.26 ml, 1.85 mmol) in N,N-dimethylformamide (6 ml) in air at room temperature. The reaction mixture was stirred at 25° C. overnight. Water (25 ml) was added, and the mixture was extracted with ethyl acetate (20 ml×3). The organic phase was washed with saturated brine (10 ml), water (25 ml), dried over sodium sulfate, and evaporated in vacuo. The residue was purified with Prep-TLC (elute: dichloromethane:methanol=25:1) to obtain crude product which was washed with methanol (4 ml) to yield the title compound as a white solid. 33 mg.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 ml×3)
  2. washThe organic phase was washed with saturated brine (10 ml), water (25 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified with Prep-TLC (elute: dichloromethane:methanol=25:1)
  6. customto obtain crude product which
  7. washwas washed with methanol (4 ml)

Sources & evidence

ORD record
ord-19e8b2dc36f94c478d0e9f7e1d7570c2
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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