Diisopropylethylamine → HCID 58017569, compound

HRID 1694388Notes

Reaction equation

HRID 1694388 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11](O)=[O:12])[CH:10]=1)[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)[CH:6]=[CH:5]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CS([O-])(=O)=O.[CH3:54][O:55][C:56]([C:58]1[CH:63]=[CH:62][C:61]([C:64]2([NH3+:67])[CH2:66][CH2:65]2)=[CH:60][CH:59]=1)=[O:57].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH:67][C:64]3([C:61]4[CH:62]=[CH:63][C:58]([C:56]([O:55][CH3:54])=[O:57])=[CH:59][CH:60]=4)[CH2:66][CH2:65]3)=[O:12])[CH:10]=1)[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)[CH:6]=[CH:5]2

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 58017570HCID 58017570, compoundHCID 867615541006037-04-2

Product 1

HCID 58017569HCID 58017569, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-fluoro-1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylic acid (218 mg, 0.65 mmol), HATU (283 mg, 0.74 mmol) and 1-[4-(methoxycarbonyl)phenyl]cyclopropanaminium methane sulfonate (374 mg, 1.3 mmol) were dissolved in DMF (4 ml), then was added Hunig's base (0.34 ml, 2.0 mmol). The reaction mixture was aged at RT overnight. The mixture was transferred to a separating funnel with EtOAc and NaHCO3 (½ sat.). The organic layer was washed with 4× brine (½ sat.), dried over MgSO4, filtered and the solvent evaporated under reduced pressure. The product was purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 9.25 (s, 1H), 7.75 (d, 2H), 7.55 (m, 4H), 7.20 (m, 3H), 6.90 (d, 2H), 6.65 (d, 1H), 5.65 (s, 2H), 3.85 (d, 3H), 1.20 (m, 2H), 0.95 (m, 2H).

Workup

  1. washThe organic layer was washed with 4× brine (½ sat.)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customThe product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5052060d9bff4df6b84fdaf262813743
Source dataset
uspto-grants-2012_04
Patent number
US08158671B2

Reaction notes

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