Hydrochloric Acid → HCID 70874026, compound

HRID 2208849Notes

Reaction equation

HRID 2208849 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:25](=[O:37])[NH:26][CH2:27][C:28]2[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=2[CH3:34])[C:5]([CH3:24])=[C:6]([N:8]([CH2:22][CH3:23])[CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:7]=1.Cl.O.C(Cl)Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:22][CH3:23])[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:5]([CH3:24])=[C:4]([CH:3]=1)[C:25]([NH:26][CH2:27][C:28]1[C:29](=[O:36])[NH:30][C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34])=[O:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 70913255HCID 70913255, compound

Product 1

HCID 70874026HCID 70874026, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-[(5-chloro-3-{[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]carbamoyl}-2-methylphenyl)(ethyl)amino]piperidine-1-carboxylate (140 mg, 0.26 mmol) in 1,4-dioxane (5 ml) at room temperature was added HCl (4M in dioxane) (1.32 ml). A gum formed after stirring for a short time which then dissolved upon the addition of deionized water (2 ml). The reaction was stirred for 21 h before being concentrated under reduced pressure to give a thick oil. DCM (3 ml) was added and a solid formed. This mixture was concentrated to give 105 mg of a yellow solid which was stirred in DCM (10 ml) for 1 hour before being filtered and dried under high vacuum in a vacuum oven for 24 hours. The sample was then dissolved in deionized water (0.2 ml) and lyophilized to give 86 mg (70%) of the title compound as a beige solid. LC-MS 100%, m/z=431.2/433.2, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.44 (bs, 1H), 7.26 (bs, 1H), 6.69 (bs, 1H), 4.55 (s, 2H), 3.53-3.34 (m, 3H), 3.28-3.08 (m, 2H), 3.01 (t, J=11.8 Hz, 2H), 2.51 (s, 3H), 2.43 (s, 3H), 2.33 (s, 3H), 2.16-1.96 (m, 2H), 1.91-1.76 (m, 2H), 0.92 (t, J=6.9 Hz, 3H).

Workup

  1. customA gum formed
  2. stirringThe reaction was stirred for 21 h
  3. concentrationbefore being concentrated under reduced pressure
  4. customto give a thick oil
  5. customa solid formed
  6. concentrationThis mixture was concentrated

Sources & evidence

ORD record
ord-65a9fa06dd68404993da06839ec919cd
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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