1,2-Dichloroethane → HCID 67108081, compound

HRID 1623795

Reaction equation

HRID 1623795 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:14][C:10]=2[C:11](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:38][C:39]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][N:40]=1>CN(C)C=O.O>[F:38][C:39]1[C:44]([NH:45][C:11](=[O:12])[C:10]2[CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][C:9]=2[O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:43][CH:42]=[CH:41][N:40]=1

Participants

7

Reactant 4

HCID 111,2-Dichloroethane2×HCID 757711-Hydroxybenzotriazole2×HCID 27628162-Fluoropyridin-3-amine2×HCID 66990482HCID 66990482, compound

Product 1

HCID 67108081HCID 67108081, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 0.12 g, 0.34 mmol), EDC (0.16 g, 0.84 mmol) and HOBT (0.13 g, 0.84 mmol) in dimethylformamide (2 ml) was stirred in air at room temperature for 1 h. 2-Fluoropyridin-3-amine (0.04 g, 0.37 mmol) was then added in one charge. The reaction mixture was stirred at 25° C. overnight. Another batch of HOBT (0.13 g, 0.84 mmol), EDC (0.161 g, 0.842 mmol) and 2-fluoropyridin-3-amine (0.04 g, 0.37 mmol) was added into the mixture and heating was continued at 40° C. for 38 hours. The reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (60 ml×3). The organic phases were combined, washed with brine (50 ml×3), dried over anhydrous MgSO4, and concentrated. The residue was purified by chromatography (silica gel, 40 g, eluent: dichloromethane/methanol=50:1, 1 L). The solid was washed by methanol (3 ml×2) and dried in vacuo to yield the title compound as a grey solid. 31 mg.

Workup

  1. additioncharge
  2. temperatureheating
  3. waitwas continued at 40° C. for 38 hours
  4. extractionextracted with ethyl acetate (60 ml×3)
  5. washwashed with brine (50 ml×3)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (silica gel, 40 g, eluent: dichloromethane/methanol=50:1, 1 L)
  9. washThe solid was washed by methanol (3 ml×2)
  10. customdried in vacuo

Sources & evidence

ORD record
ord-1432107721e24f09a13cf0c66b754ca1
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Linked notes

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