Hydrochloric Acid → HCID 178513244, compound

HRID 2046023Notes

Reaction equation

HRID 2046023 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-1bcd95a96da444c892232b2f4a3ba4a0
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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