Water → HCID 67070043, compound

HRID 2390870Notes

Reaction equation

HRID 2390870 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[C:17]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:18]([O:31][CH3:32])=[C:19]([NH:21][C:22]([C:24]3[N:25]=[N:26][C:27](Cl)=[CH:28][CH:29]=3)=[O:23])[CH:20]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:37][C:38]([F:42])([F:41])[CH2:39][NH2:40].O>CN1C(=O)CCC1>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[C:17]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:18]([O:31][CH3:32])=[C:19]([NH:21][C:22]([C:24]3[N:25]=[N:26][C:27]([NH:40][CH2:39][C:38]([F:42])([F:41])[F:37])=[CH:28][CH:29]=3)=[O:23])[CH:20]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 86638345HCID 86638345, compound

Product 1

HCID 67070043HCID 67070043, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

step 2—A solution of 312 (0.059 g, 0.1 mmol) and 2,2,2-trifluoroethylamine (0.5 mL) in NMP (1.0 mL) in a screw-capped test tube was heated to 100° C. After 18 h the solution was cooled to RT poured into H2O and extracted with EtOAc. The combined organics were washed sequentially with H2O and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane (6% to 60% EtOAc) to afford 0.029 g (37%) 6-(2,2,2-trifluoro-ethylamino)-pyridazine-3-carboxylic acid [5-(2-benzyloxy-pyridin-3-yl)-3-tert-butyl-2-methoxy-phenyl]-amide (314) as an oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed sequentially with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with an EtOAc/hexane (6% to 60% EtOAc)

Sources & evidence

ORD record
ord-3af448e54f374523ba142ba018e3f65a
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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