1,2-Dichloroethane → HCID 86690827, compound

HRID 1465525Notes

Reaction equation

HRID 1465525 reaction equation
Cl.[C:2]([OH:10])(=O)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[NH2:32][C:33]1[S:34][CH:35]=[C:36]([C:38]2[C:43]([CH3:44])=[CH:42][C:41]([OH:45])=[CH:40][C:39]=2[CH3:46])[N:37]=1>CN(C=O)C>[OH:45][C:41]1[CH:40]=[C:39]([CH3:46])[C:38]([C:36]2[N:37]=[C:33]([NH:32][C:2](=[O:10])[C:3]3[CH:4]=[CH:5][N:6]=[CH:7][CH:8]=3)[S:34][CH:35]=2)=[C:43]([CH3:44])[CH:42]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 57455229HCID 57455229, compoundHCID 866908264-(2-Aminothiazol-4-yl)-3,5-dimethylphenol

Product 1

HCID 86690827HCID 86690827, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of isonicotinic acid hydrochloride (1.48 g, 10.0 mmol, 1.2 equiv) in DMF was added EDC (3.90 g, 2.0 equiv), HOBt (2.7 g, 2.0 equiv) and NEt3 (3.03 g, 3.0 equiv). After being stirred at room temperature for 1.0 h, the solution was added with 4-(2-aminothiazol-4-yl)-3,5-dimethylphenol (5-2, 2.2 g, 1.0 equiv). The reaction mixture was stirred at room temperature overnight. The solution was concentrated and the residue was re-dissolved in EtOAc. The solution was washed with brine, dried over MgSO4, and concentrated under reduced pressure to give brown solid. The brown solid was washed with 50% EtOAc in hexanes to give 5-3 (2.08 g) as white solids in 64% yield: 1H NMR (500 MHz, CDCl3) δ 9.29 (s, 1 H), 8.80 (d, 2 H), 7.98 (d, 2 H), 7.06 (s, 1 H), 6.51 (s, 2 H), 2.01 (s, 6H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. concentrationThe solution was concentrated
  3. dissolutionthe residue was re-dissolved in EtOAc
  4. washThe solution was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto give brown solid
  8. washThe brown solid was washed with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-8b3db2d941044bb2bd60b1f308a50541
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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