Hydrochloric Acid → HCID 178513244, compound

HRID 717607Notes

Reaction equation

HRID 717607 reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][C:6]=2[CH:7]=1.Cl.[NH2:15][OH:16].C(N(CC)C(C)C)(C)C>C(O)C>[OH:16][NH:15][C:12]([C:9]1[CH:10]=[CH:11][C:5]2[O:4][C:3]([CH2:2][OH:1])=[CH:7][C:6]=2[CH:8]=1)=[NH:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 81531DiisopropylethylamineHCID 12813635HCID 12813635, compound

Product 1

HCID 178513244HCID 178513244, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
71 °C

Procedure

A mixture of the product of Step B (0.22 g; 1.27 mmol) and HCl×NH2OH (0.18 g; 2.59 mmol) and N,N-diisopropylethylamine (DIPEA) (0.67 ml; 3.82 mmol) in ethanol (EtOH) (2 ml) was stirred for 3 h at ˜71° C. The solvents were removed in vacuo and the residue was treated with H2O (3 ml) and the product was taken up by EtOAc (3×15 ml). The combined organic phase was washed with brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title compound (0.2 g; 76%), as colourless solid, which was used in the next step without further purification.

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe residue was treated with H2O (3 ml)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customfiltrate evaporated to dryness

Sources & evidence

ORD record
ord-924df916665b471dad0c01e8555d92a3
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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