Diisopropylethylamine → tert-Butyl 4,4,4-trifluoro-1-oxo-1-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)butan-2-ylcarbamate

HRID 524999Notes

Reaction equation

HRID 524999 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].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.[NH2:51][N:52]1[CH:56]=[CH:55][CH:54]=[C:53]1[C:57]([NH:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=[O:58]>CN(C)C=O.ClCCl>[F:15][C:14]([F:17])([F:16])[CH2:13][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10](=[O:12])[NH:51][N:52]1[CH:56]=[CH:55][CH:54]=[C:53]1[C:57](=[O:58])[NH:59][C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=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 120980572-(((Tert-butoxy)carbonyl)amino)-4,4,4-trifluorobutanoic acidHCID 709224541-amino-N-phenyl-1H-pyrrole-2-carboxamide

Product 1

HCID 86722021tert-Butyl 4,4,4-trifluoro-1-oxo-1-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)butan-2-ylcarbamateYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

421 mg (1.64 mmol) of 2-(tert-butoxycarbonylamino)-4,4,4-trifluorobutanoic acid were suspended in a mixture of N,N-dimethylformamide (5 mL) and dichloromethane (5 mL) and HATU (624 mg, 1.64 mmol) and DIEA (286 μl, 1.64 mmol) were added. The resulting suspension was stirred at room temperature for 2 hours and then 1-amino-N-phenyl-1H-pyrrole-2-carboxamide (300 mg, 1.49 mmol) was added. The resulting solution was stirred at room temperature overnight and the dichloromethane was removed in vacuum. 25 mL of water were added to the remaining solution and, after vigorous stirring, the solid that formed was filtered and washed with water. 582 mg (89% yield) of the title compound were obtained as a white solid.

Workup

  1. additionwere added
  2. stirringThe resulting solution was stirred at room temperature overnight
  3. customthe dichloromethane was removed in vacuum
  4. addition25 mL of water were added to the remaining solution
  5. customafter vigorous stirring, the solid that formed
  6. filtrationwas filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-a38dff65ca9e494eb2d74d0aa6b7803f
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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