Diisopropylethylamine → HCID 86729584, compound

HRID 574197Notes

Reaction equation

HRID 574197 reaction equation
[CH2:1]([O:8][C:9]([CH3:17])([C:13]([F:16])([F:15])[F:14])[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:51]([C:53]([C:55]1[C:60]([NH:61][C:62](=[O:68])[O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[CH:59][C:58]([C:69]([F:72])([F:71])[F:70])=[C:57]([O:73][CH3:74])[N:56]=1)=[O:54])[NH2:52]>CN(C=O)C.O>[CH2:1]([O:8][C:9]([CH3:17])([C:13]([F:16])([F:15])[F:14])[C:10]([NH:52][NH:51][C:53]([C:55]1[C:60]([NH:61][C:62](=[O:68])[O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[CH:59][C:58]([C:69]([F:70])([F:71])[F:72])=[C:57]([O:73][CH3:74])[N:56]=1)=[O:54])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86729585HCID 86729585, compoundHCID 86729586HCID 86729586, compound

Product 1

HCID 86729584HCID 86729584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(benzyloxy)-3,3,3-trifluoro-2-methylpropanoic acid (Int. D) (0.709 g, 2.85 mmol) in DMF (15 ml) was added HATU (1.303 g, 3.43 mmol) followed by DIPEA (0.598 ml, 3.43 mmol). After 30 mins, tert-butyl 2-(hydrazinecarbonyl)-6-methoxy-5-(trifluoromethyl)pyridin-3-ylcarbamate (Int. C) (1 g, 2.85 mmol) was added and the reaction mixture was stirred at RT for 3 h. The mixture was poured into water and the product extracted with EtOAc. The organic portion was washed with 1 MHCl, brine, dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with 0% to 50% EtOAc in iso-hexane afforded the title compound:

Workup

  1. extractionthe product extracted with EtOAc
  2. washThe organic portion was washed with 1 MHCl, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica eluting with 0% to 50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-262b4a23dc3e4f439e38dd118aaf554d
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

Loading…