Diisopropylethylamine → HCID 70874145, compound

HRID 2208866Notes

Reaction equation

HRID 2208866 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH3:20])[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([CH2:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[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.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH3:20])[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([CH2:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([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:9]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 70874152HCID 70874152, compound

Product 1

HCID 70874145HCID 70874145, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2-ethyl-3-[methyl(oxan-4-yl)amino]benzoic acid (100 mg, 0.34 mmol) in DMF (2 ml) at room temperature under nitrogen was added HBTU (153 mg, 0.4 mmol) followed by N-ethyl-N-(propan-2-yl)propan-2-amine (88 μl, 0.5 mmol) and 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one (89%, 63 mg, 0.37 mmol). After stirring for 3 hours at room temperature EtOAc (30 ml) was added to the reaction mixture and this was then washed with deionized water (5 ml) followed by saturated NaHCO3(aq) (3×5 ml). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by FCC (5 g silica, Isolute cartridge, gradient of eluents; 100% DCM to 96:4 DCM:MeOH) to give 94 mg (65%) of the title compound as an off-white solid. LC-MS 95%, m/z=432.1/434.1, 1H NMR (500 MHz, Chloroform-d) δ ppm 11.34 (s, 1H), 7.14-7.08 (m, 2H), 7.03 (d, J=2.0 Hz, 1H), 5.95 (s, 1H), 4.52 (d, J=5.8 Hz, 2H), 3.96 (d, J=11.2 Hz, 2H), 3.33 (td, J=11.4, 2.3 Hz, 2H), 2.96-2.85 (m, 1H), 2.79 (q, J=7.4 Hz, 2H), 2.58 (s, 3H), 2.39 (s, 3H), 2.23 (s, 3H), 1.73-1.62 (m, 4H), 1.05 (t, J=7.4 Hz, 3H).

Workup

  1. additionwas added to the reaction mixture
  2. washthis was then washed with deionized water (5 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by FCC (5 g silica, Isolute cartridge, gradient of eluents; 100% DCM to 96:4 DCM:MeOH)

Sources & evidence

ORD record
ord-74e279be26cc4e0e8955ca74ee43dff4
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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