1,2-Dichloroethane → HCID 18516133, compound

HRID 1977410Notes

Reaction equation

HRID 1977410 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14](/[CH:16]=[CH:17]/[C:18](O)=[O:19])=[CH:15][C:8]=23)=[CH:4][CH:3]=1.O.O[N:25]1C2C=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14](/[CH:16]=[CH:17]/[C:18]([NH2:25])=[O:19])=[CH:15][C:8]=23)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 18516263HCID 18516263, compound

Product 1

HCID 18516133HCID 18516133, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 91C (51.5 mg, 0.155 mmol), N-hydroxybenzotriazole monohydrate (34.5 mg, 0.225 mmol), 4-methylmorpholine (47 mg, 0.464 mmol) and NH4CN (31.6 mg, 0.591 mmol) in DMF (1 mL) at 0° C. was treated with EDC (45.0 mg, 0.235 mmol), stirred at 0° C. for 4 hours and at room temperature for 10 hours, treated with chloroform (5 mL), washed sequentially with 1M NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel with 5% methanol/dichloromethane to provide the title compound.

Workup

  1. washwashed sequentially with 1M NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-a1ebbce542e64179a43c1b26739fdf3a
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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