Diethanolamine → HCID 71533325, compound

HRID 2173710Notes

Reaction equation

HRID 2173710 reaction equation
[N:1]1[NH:2][C:3]([NH:6][C:7]([C:9]2[C:14]([NH2:15])=[N:13][C:12]([C:16]([F:19])([F:18])[F:17])=[C:11](Br)[N:10]=2)=[O:8])=[CH:4][CH:5]=1.[NH:21]([CH2:25]CO)[CH2:22]CO>CN(C=O)C>[N:1]1[NH:2][C:3]([NH:6][C:7]([C:9]2[C:14]([NH2:15])=[N:13][C:12]([C:16]([F:19])([F:18])[F:17])=[C:11]([N:21]([CH3:25])[CH3:22])[N:10]=2)=[O:8])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 71533263HCID 71533263, compound

Product 1

HCID 71533325HCID 71533325, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring solution of 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (2H-pyrazol-3-yl)-amide (Ex. 7)(50 mg, 0.142 mmol) in dry DMF (5 ml), diethanolamine (37.4 mg, 0.356 mmol) was added. The resulting solution was heated at 100° C. using microwave radiation for 66 hours. The reaction mixture was partitioned between EtOAc (20 ml) and water (20 ml), and the phases separated. The organic phase was washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo to give an orange solid. Purification of the crude product by chromatography on silica eluting with iso-hexane/EtOAc (gradient of 0 to 50% EtOAc) yielded the title compound as a yellow solid.

Workup

  1. customfor 66 hours
  2. customThe reaction mixture was partitioned between EtOAc (20 ml) and water (20 ml)
  3. customthe phases separated
  4. washThe organic phase was washed with brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give an orange solid
  8. customPurification of the crude product by chromatography on silica eluting with iso-hexane/EtOAc (gradient of 0 to 50% EtOAc)

Sources & evidence

ORD record
ord-94d698fc57624c8dacbbec3de796c58b
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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