Triethylamine → HCID 17751589, compound

HRID 1099277Notes

Reaction equation

HRID 1099277 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=3)[CH:9]=[C:10]([C:11](=[O:13])[CH3:12])[N:6]2[N:5]=[CH:4][N:3]=1.C1([O:27][C:28](=O)[NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[N:31]=2)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C.CS(C)=O>[C:11]([C:10]1[N:6]2[C:7]([C:2]([NH2:1])=[N:3][CH:4]=[N:5]2)=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:28]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:38])([F:37])[F:39])[N:31]=3)=[O:27])=[CH:16][CH:15]=2)[CH:9]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 59232086Ethanone, 1-[4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]-HCID 67079715HCID 67079715, compound

Product 1

HCID 17751589HCID 17751589, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]ethanone (50.0 mg, 0.19 mmol), phenyl[6-(trifluoromethyl)pyridin-2-yl]carbamate (105.6 mg, 0.37 mmol), and triethylamine (0.10 mL, 0.75 mmol) in DMF (2 mL) was stirred overnight resulting in formation of a precipitate. The mixture was diluted with DMSO (1 mL) and then the solid was collected by filtration, washed with MeOH, and air-dried to give 53.0 mg (62%) of the title compound. 1H-NMR (DMSO-d6) δ 9.87 (s, 1 H), 9.71 (s, 1 H), 9.60 (d, J=3.2 Hz, 1H), 8.34 (d, J=3.3, 1 H), 8.10 (s, 1 H), 8.04-8.02 (m, 4 H), 7.76 (s, 1 H), 7.59 (d, J=8.7 Hz, 2 H), 7.52-7.50 (m, 1 H), 2.64 (s, 3 H); MS [M+H]+=456.1; LCMS RT=3.25 min.

Workup

  1. customresulting in formation of a precipitate
  2. filtrationthe solid was collected by filtration
  3. washwashed with MeOH
  4. customair-dried

Sources & evidence

ORD record
ord-117bd161759a4c01ba8981c89abd1d79
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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