Triethylamine → HCID 90460918, compound

HRID 588763Notes

Reaction equation

HRID 588763 reaction equation
[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5](=[O:13])[N:6]([CH2:8][CH2:9][C:10]([OH:12])=O)[CH:7]=1.[N:15]1([C:21](=[O:24])[CH:22]=[CH2:23])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[C:21]([N:15]1[CH2:20][CH2:19][N:18]([C:10](=[O:12])[CH2:9][CH2:8][N:6]2[CH:7]=[C:2]([Br:1])[C:3]([CH3:14])=[CH:4][C:5]2=[O:13])[CH2:17][CH2:16]1)(=[O:24])[CH:22]=[CH2:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11963076HCID 11963076, compoundHCID 82146618HCID 82146618, compound

Product 1

HCID 90460918HCID 90460918, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(5-Bromo-4-methyl-2-oxopyridin-1(2H)-yl)propanoic acid (112 mg, 0.43 mmol), 1-(piperazin-1-yl)prop-2-en-1-one (80 mg, 0.43 mmol), HATU (163 mg, 0.43 mmol) and Et3N (0.2 mL, 1.43 mmol) in DMF (5 mL) was stirred at room temperature for 2 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via Isolera One (silica cartridge, 0-6% MeOH/DCM) to afford the desired product (22.8 mg, 14 yield). 1H NMR (300 MHz, CDCl3) δ: 7.73 (s, 1H), 6.55 (dd, J=10.5, 16.7 Hz, 1H), 6.46 (s, 1H), 6.32 (dd, J=1.8, 16.8 Hz, 1H), 5.75 (dd, J=1.8, 10.5 Hz, 1H), 4.20 (t, J=6.0 Hz, 2H), 3.4-3.6 (m, 8H), 2.86 (t, J=6.0 Hz, 2H), 2.22 (s, 3H). ESI-MS m/z: 382.05 [M+H]+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via Isolera One (silica cartridge, 0-6% MeOH/DCM)

Sources & evidence

ORD record
ord-915a7cb503dd4812beb375d5909921a5
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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