Diisopropylethylamine → HCID 86648144, compound

HRID 239854Notes

Reaction equation

HRID 239854 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:13][C@@H:14]([CH2:18][CH:19]([Cl:21])[Cl:20])[C:15]([OH:17])=O)[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[Cl-].[C:23]([C@@H:25]([NH3+:36])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][C:28]=1[F:35])#[N:24].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.C(=O)([O-])O.[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:13][C@@H:14]([CH2:18][CH:19]([Cl:21])[Cl:20])[C:15]([NH:36][C@H:25]([C:23]#[N:24])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][C:28]=2[F:35])=[O:17])[C:9]([F:10])([F:11])[F:12])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68776901HCID 68776901, compoundHCID 86609688HCID 86609688, compound

Product 1

HCID 86648144HCID 86648144, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2S)-2-{[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]amino}-4,4-dichlorobutanoic acid (120 mg) and (1S)-1-cyano-2-(4-cyano-2-fluorophenyl)ethanaminium chloride (66 mg) were dissolved in DMF (1.5 ml) and HATU (223 mg) was added. The reaction mixture was stirred at room temperature for 5 min and Hunig's base (204 μL) was added. The solution was stirred for 18 hours. The mixture was poured onto an aqueous sodium hydrogen carbonate (saturated, 20 ml) and water (20 ml). The mixture was stirred in an erlenmeyer flask for 10 min. The aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried on MgSO4. It was concentrated under reduced pressure. The crude product was purified by flash (eluted with 20:80 to 55:45 EtOAc/hexanes).

Workup

  1. stirringThe solution was stirred for 18 hours
  2. stirringThe mixture was stirred in an erlenmeyer flask for 10 min
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. customdried on MgSO4
  6. concentrationIt was concentrated under reduced pressure
  7. customThe crude product was purified by flash (eluted with 20:80 to 55:45 EtOAc/hexanes)

Sources & evidence

ORD record
ord-3dc1282e13904d98b863efcd6ece4b32
Source dataset
uspto-grants-2014_02
Patent number
US08642799B2

Reaction notes

Loading…