Diisopropylethylamine → 5-methoxy-N-[[2-(trifluoromethyl)-1H-indol-5-yl]methyl]pyrazine-2-carboxamide

HRID 388391Notes

Reaction equation

HRID 388391 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][O:26][C:27]1[N:28]=[CH:29][C:30]([C:33]([OH:35])=O)=[N:31][CH:32]=1.CCN(C(C)C)C(C)C.[F:45][C:46]([F:59])([F:58])[C:47]1[NH:48][C:49]2[C:54]([CH:55]=1)=[CH:53][C:52]([CH2:56][NH2:57])=[CH:51][CH:50]=2>CN(C=O)C>[CH3:25][O:26][C:27]1[N:28]=[CH:29][C:30]([C:33]([NH:57][CH2:56][C:52]2[CH:53]=[C:54]3[C:49](=[CH:50][CH:51]=2)[NH:48][C:47]([C:46]([F:59])([F:45])[F:58])=[CH:55]3)=[O:35])=[N:31][CH:32]=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 457898115-Methoxy-2-pyrazinecarboxylic acidHCID 58126817(2-(Trifluoromethyl)-1h-indol-5-yl)methanamine2×

Product 1

HCID 444662015-methoxy-N-[[2-(trifluoromethyl)-1H-indol-5-yl]methyl]pyrazine-2-carboxamideYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred solution of HATU (121 mg, 0.319 mmol) in DMF (1 ml) was added 5-(methyloxy)-2-pyrazinecarboxylic acid (AniChem LLC; 49.2 mg, 0.319 mmol) in DMF (0.5 ml), followed by DIPEA (0.084 ml, 0.479 mmol) and finally {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 4, 40 mg, 0.160 mmol) in DMF (1 ml). The solution was stirred for 24 hrs. DMF was removed using a rotary evaporator followed by addition of DCM and sodium bicarbonate solution. The mixture was poured through a phase separation cartridge. The organic layer was evaporated to dryness and purified using MDAP to give the title compound as a white solid (34 mg);

Workup

  1. customDMF was removed
  2. customa rotary evaporator
  3. additionfollowed by addition of DCM and sodium bicarbonate solution
  4. additionThe mixture was poured through a phase separation cartridge
  5. customThe organic layer was evaporated to dryness
  6. custompurified

Sources & evidence

ORD record
ord-1fbdf40e24c04bc5a0a45ec630b981ef
Source dataset
uspto-grants-2013_02
Patent number
US08377941B2

Reaction notes

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