1,2-Dichloroethane → HCID 59507491, compound

HRID 1043813Notes

Reaction equation

HRID 1043813 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([OH:10])=O)[N:6]=1.[CH:11]1[CH:16]=[N:15][C:14]2N(O)N=N[C:13]=2C=1.C(Cl)CCl.N(CC)CC>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([N:15]([CH2:16][CH3:11])[CH2:14][CH3:13])=[O:10])[N:6]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 34665(2-Amino-1,3-thiazol-4-yl)acetic acidHCID 181649HOAt

Product 1

HCID 59507491HCID 59507491, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-(2-aminothiazol-4-yl)acetic acid (1 eq), HOAT (1 eq), EDC (1.1 eq), TEA (1 eq) and HNEt2 (1 eq) in DMA was stirred at room temperature for 6 hours. The reaction mixture was then quenched with H2O and concentrated. The residue was dissolved in a stirred 4:1 mixture of EtOAc and NaHCO3(sat.). The two phases were separated and the organic solution was washed with brine, dried over Na2SO4 and concentrated to dryness. The resulting solid was washed twice with Et2O and dried to yield the desired product as a white solid. LC/MS (m/z): 214.0 (MH+), Rt 1.13 minutes.

Workup

  1. customThe reaction mixture was then quenched with H2O
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in
  4. stirringa stirred
  5. addition4:1 mixture of EtOAc and NaHCO3(sat.)
  6. customThe two phases were separated
  7. washthe organic solution was washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to dryness
  10. washThe resulting solid was washed twice with Et2O
  11. customdried

Sources & evidence

ORD record
ord-dfe0886cbcce4b469b2f6e1b58525d71
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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