Diisopropylethylamine → HCID 70873923, compound

HRID 2208835Notes

Reaction equation

HRID 2208835 reaction equation
[CH2:1]([N:8]([CH2:19][CH3:20])[C:9]1[C:10]([CH3:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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.[NH2:54][CH2:55][C:56]1[C:57](=[O:64])[NH:58][C:59]([CH3:63])=[CH:60][C:61]=1[CH3:62]>CN(C=O)C.O>[CH2:1]([N:8]([CH2:19][CH3:20])[C:9]1[C:10]([CH3:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH:54][CH2:55][C:56]1[C:57](=[O:64])[NH:58][C:59]([CH3:63])=[CH:60][C:61]=1[CH3:62])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

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 70873862HCID 70873862, compound

Product 1

HCID 70873923HCID 70873923, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (3-[benzyl(ethyl)amino]-2-methylbenzoic acid (91% purity, 296 mg, 1.0 mmol) in DMF (10 ml) was added DIPEA (440 μl, 2.5 mmol) and HATU (570 mg, 1.5 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%, 222 mg, 1.3 mmol) was added and the reaction was stirred at room temperature for 16 h. The reaction mixture was then poured onto 150 ml of water and stirred for 20 min. The product was filtered, air dried under vacuum and then purified using RP-HPLC. The resulting solid was triturated with diethyl ether and isolated by filtration to afford the title compound as an off white solid (86 mg, 21%). LC-MS 99%, m/z=404.3, 1H NMR (500 MHz, Chloroform-d) δ 12.04 (s, 1H), 7.33-7.23 (m, 4H), 7.21 (t, J=6.8 Hz, 1H), 7.14-7.05 (m, 3H), 7.05-6.99 (m, 1H), 5.92 (s, 1H), 4.53 (d, J=5.9 Hz, 2H), 4.06 (s, 2H), 2.92 (q, J=6.9 Hz, 2H), 2.41 (s, 3H), 2.39 (s, 3H), 2.16 (s, 3H), 0.92 (t, J=7.0 Hz, 3H).

Workup

  1. additionwas added
  2. stirringstirred for 20 min
  3. filtrationThe product was filtered
  4. customair dried under vacuum
  5. custompurified
  6. customThe resulting solid was triturated with diethyl ether
  7. customisolated by filtration

Sources & evidence

ORD record
ord-8252ef93c3fc4701825cc0e9a7a4748a
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…