Diisopropylethylamine → HCID 86620691, compound

HRID 913650Notes

Reaction equation

HRID 913650 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:47]([C:49]1[C:50]([C:65]([F:68])([F:67])[F:66])=[C:51]2[C:55](=[CH:56][CH:57]=1)[N:54]([CH2:58]/[C:59](=[N:62]/[H])/[NH:60]O)[C:53]([CH3:64])=[CH:52]2)#[N:48]>CC#N>[CH3:64][C:53]1[N:54]([CH2:58][C:59]2[N:62]=[C:9]([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:13])[F:12])[N:8]=3)[O:11][N:60]=2)[C:55]2[C:51]([CH:52]=1)=[C:50]([C:65]([F:67])([F:66])[F:68])[C:49]([C:47]#[N:48])=[CH:57][CH:56]=2

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 147614536-(Trifluoromethyl)pyridine-2-carboxylic acidHCID 178506476HCID 178506476, compound

Product 1

HCID 86620691HCID 86620691, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-(trifluoromethyl)-2-pyridinecarboxylic acid (ref: European Journal of Organic Chemistry (2003), (8), 1569-1575) (0.032 g, 0.169 mmol) in 2 mL of MeCN was added DIEA (0.022 g, 0.169 mmol) and HATU (0.064 g, 0.169 mmol). After stirring at rt for 2 min, (1Z)-2-[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (0.050 g, 0.169 mmol) was added. After stirring at rt for 30 min, the mixture was heated in a sealed tube at 150° C. for 1.5 h. Upon cooling, the mixture was concentrated to dryness and the residue was purified by silica gel chromatography using a 5-50% EtOAc-hexanes gradient. The product was crystallized from CH2Cl2-hexanes to afford the title compound as a white solid (0.035 g, 46% yield): MS (ES) m/z 452 (M+1).

Workup

  1. stirringAfter stirring at rt for 30 min
  2. temperaturethe mixture was heated in a sealed tube at 150° C. for 1.5 h
  3. temperatureUpon cooling
  4. concentrationthe mixture was concentrated to dryness
  5. customthe residue was purified by silica gel chromatography
  6. customThe product was crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-a6ad883bd20d492bbaa4f264ed45f4d9
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

Loading…