1,2-Dichloroethane → HCID 68494793, compound

HRID 888376Notes

Reaction equation

HRID 888376 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([CH:16]=2)[C:13]([OH:15])=[O:14])=[N:6][CH:7]=1.CN.C(Cl)CCl.C1C=C[C:26]2N(O)N=N[C:27]=2[CH:28]=1.[CH:33](N(C(C)C)CC)(C)C.[CH3:42][N:43](C)[CH:44]=[O:45]>O>[CH3:42][NH:43][C:44]([C:10]1[CH:11]=[C:12]([CH:16]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[CH:9]=1)[C:13]([O:15][C:27]([CH3:26])([CH3:28])[CH3:33])=[O:14])=[O:45]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86646756HCID 86646756, compound

Product 1

HCID 68494793HCID 68494793, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-tert-butoxycarbonyl)-5-(5-methylpyridin-2-yl)benzoic acid (1.15 g, 3.67 mmol) in N,N-dimethylformamide (36 mL) were added methanamine (5.51 mL, 11.01 mmol), EDC (2.11 g, 11.01 mmol), HOBT (1.12 g, 7.34 mmol) and diisopropylethylamine (2.56 mL, 14.68 mmol). The reaction mixture was stirred at ambient temperature. After 18 h, water was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with water (2×), brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→30% hexanes/ethyl acetate) gave the title compound. MS 327.1 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with water (2×), brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% hexanes→30% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-2371878966dd4a23b661c438b8739736
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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