Diisopropylethylamine → HCID 70913562, compound

HRID 2208825Notes

Reaction equation

HRID 2208825 reaction equation
[CH2:1]([N:3]([CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:4]1[C:5]([CH3:13])=[C:6]([C:10]([OH:12])=O)[CH:7]=[N:8][CH:9]=1)[CH3:2].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.[NH2:53][CH2:54][C:55]1[C:56](=[O:63])[NH:57][C:58]([CH3:62])=[CH:59][C:60]=1[CH3:61]>CN(C=O)C.O>[CH3:61][C:60]1[CH:59]=[C:58]([CH3:62])[NH:57][C:56](=[O:63])[C:55]=1[CH2:54][NH:53][C:10]([C:6]1[CH:7]=[N:8][CH:9]=[C:4]([N:3]([CH2:1][CH3:2])[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]=1[CH3:13])=[O:12]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 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)HCID 70873624HCID 70873624, compound

Product 1

HCID 70913562HCID 70913562, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-[ethyl(oxan-4-yl)amino]-4-methylpyridine-3-carboxylic acid (300 mg, 1.13 mmol) in DMF (10 ml) was added DIPEA (395 μl, 2.27 mmol) and HATU (518 mg, 1.36 mmol). The reaction was stirred at room temperature for 5 min after which time 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one (89%, 214 mg, 1.25 mmol) was added and the reaction was stirred at room temperature for 18 h. The reaction mixture was then poured onto 500 ml of water and the product was extracted into EtOAc (3×200 ml), the combined organic phase was washed with brine (2×100 ml), dried (Na2SO4) and evaporated. The crude product was then purified using preparative-HPLC and the resulting solid was triturated with diethyl ether and isolated by filtration to afford the title compound as an off white solid (115 mg, 25%). LC-MS 100%, m/z=399.2, 1H NMR (500 MHz, Acetone) δ 10.97 (s, 1H), 8.32 (s, 1H), 8.22 (s, 1H), 7.73 (s, 1H), 5.92 (s, 1H), 4.41 (d, J=5.3 Hz, 2H), 3.85 (dd, J=11.3, 3.0 Hz, 2H), 3.28 (td, J=11.7, 1.9 Hz, 2H), 3.15 (q, J=7.1 Hz, 2H), 3.09 (ddd, J=11.1, 7.2, 3.9 Hz, 1H), 2.32 (d, J=1.5 Hz, 6H), 2.23 (s, 3H), 1.69 (dd, J=12.6, 1.7 Hz, 2H), 1.55 (ddd, J=24.3, 12.2, 4.4 Hz, 2H), 0.85 (t, J=7.1 Hz, 3H).

Workup

  1. additionwas added
  2. extractionthe product was extracted into EtOAc (3×200 ml)
  3. washthe combined organic phase was washed with brine (2×100 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product was then purified
  7. customthe resulting solid was triturated with diethyl ether
  8. customisolated by filtration

Sources & evidence

ORD record
ord-75044c4232284d10a3b4b2ac22eb3743
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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