Diisopropylethylamine → HCID 70873922, compound

HRID 2208828Notes

Reaction equation

HRID 2208828 reaction equation
[F:1][C:2]1[C:3]([C:11]([F:14])([F:13])[F:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.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.[NH2:48][CH2:49][C:50]1[C:51](=[O:58])[NH:52][C:53]([CH3:57])=[CH:54][C:55]=1[CH3:56]>CN(C=O)C>[CH3:56][C:55]1[CH:54]=[C:53]([CH3:57])[NH:52][C:51](=[O:58])[C:50]=1[CH2:49][NH:48][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27747803-Fluoro-2-(trifluoromethyl)benzoic acidHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 70873922HCID 70873922, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-fluoro-2-(trifluoromethyl)benzoic acid (1.00 g, 4.81 mmol) in DMF (25 ml) cooled in an ice bath was added HATU (2.19 g, 5.77 mmol) and DIPEA (1.67 ml, 9.61 mmol). The reaction was stirred at 0° C. for 5 min after which time 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one (89%, 904 mg, 5.29 mmol) was added and the reaction was warmed room temperature for 4 h. The reaction mixture was then poured onto distilled water (300 ml) and stirred for 1 h after which time the precipitate was collected via vacuum filtration using microfibre paper. The resulting solid was triturated using diethyl ether and filtered to afford the title compound as a pale brown solid (1.19 g, 72%). LC-MS 100%, m/z=343.0, 1H NMR (500 MHz, DMSO) δ 11.48 (s, 1H), 8.54 (t, J=4.8 Hz, 1H), 7.71 (dd, J=13.3, 8.0 Hz, 1H), 7.56-7.45 (m, 1H), 7.20 (d, J=7.6 Hz, 1H), 5.86 (s, 1H), 4.25 (d, J=4.9 Hz, 2H), 2.18 (s, 3H), 2.11 (s, 3H).

Workup

  1. additionwas added
  2. additionThe reaction mixture was then poured
  3. distillationonto distilled water (300 ml)
  4. filtrationwas collected via vacuum filtration
  5. customThe resulting solid was triturated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-da9110b0537c47a184a16f242fbda69d
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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