Diisopropylethylamine → HCID 44462841, compound

HRID 388396Notes

Reaction equation

HRID 388396 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[N:7][C:6]([C:9]([OH:11])=O)=[CH:5][CH:4]=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.Cl.[F:48][C:49]([F:62])([F:61])[C:50]1[NH:51][C:52]2[C:57]([CH:58]=1)=[CH:56][C:55]([CH2:59][NH2:60])=[CH:54][CH:53]=2>C(#N)C>[F:12][C:2]([F:1])([F:13])[C:3]1[N:8]=[N:7][C:6]([C:9]([NH:60][CH2:59][C:55]2[CH:56]=[C:57]3[C:52](=[CH:53][CH:54]=2)[NH:51][C:50]([C:49]([F:62])([F:48])[F:61])=[CH:58]3)=[O:11])=[CH:5][CH:4]=1

Participants

6

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 581268206-(trifluoromethyl)pyridazine-3-carboxylic acid2×HCID 669093631H-Indole-5-methanamine, 2-(trifluoromethyl)-, hydrochloride (1:1)2×

Product 1

HCID 44462841HCID 44462841, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-(trifluoromethyl)-3-pyridazinecarboxylic acid (Intermediate 9, 60 mg, 0.312 mmol), HATU (131 mg, 0.344 mmol) and DIPEA (0.164 ml, 0.937 mmol) in acetonitrile (3 ml) was stirred at room temperature under argon for 15 mins and then treated with {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine hydrochloride (Intermediate 5, 78 mg, 0.312 mmol). The reaction mixture was stirred for 18 hrs and evaporated under reduced pressure to remove the acetonitrile. The residue was dissolved in DCM and washed with water. The organic solution was dried over MgSO4 and evaporated under reduced pressure to afford the crude product which was purified by MDAP the title compound (39 mg) as a pale solid;

Workup

  1. customevaporated under reduced pressure
  2. customto remove the acetonitrile
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with water
  5. dry with materialThe organic solution was dried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4ac2fe814afa4d03ad34ae06317e8c92
Source dataset
uspto-grants-2013_02
Patent number
US08377941B2

Reaction notes

Loading…