Hydrochloric Acid → HCID 86671939, compound

HRID 84257Notes

Reaction equation

HRID 84257 reaction equation
[CH3:1][C@@:2]([S:42]([CH3:45])(=[O:44])=[O:43])([CH2:13][CH2:14][N:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH:30]3[CH2:33][CH:32]([O:34]C4CCCCO4)[CH2:31]3)=[CH:23][CH:22]=2)=[CH:17][C:16]1=[O:41])[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl>O1CCOCC1.CO.CCOCC>[OH:6][NH:5][C:3](=[O:4])[C@:2]([CH3:1])([S:42]([CH3:45])(=[O:44])=[O:43])[CH2:13][CH2:14][N:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH:30]3[CH2:33][CH:32]([OH:34])[CH2:31]3)=[CH:23][CH:22]=2)=[CH:17][C:16]1=[O:41]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86671940HCID 86671940, compound

Product 1

HCID 86671939HCID 86671939, compoundYield 80.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To (2R)-2-methyl-2-(methylsulfonyl)-4-[2-oxo-4-(4-{2-[3-(tetrahydro-2H-pyran-2-yloxy)cyclobutyl]ethoxy}phenyl)pyridin-1(2H)-yl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (386 mg, 0.597 mmol) was added 4 N hydrogen chloride in dioxane (6.0 mL) and methanol (0.60 mL). The reaction was stirred for 30 minutes and then evaporated in vacuo to give a yellow oil. The residue was dissolved in a minimal amount of methanol (0.50 mL) and diluted with ether to give a yellow precipitate. This suspension was stirred overnight at room temperature. The solid was allowed to settle and the liquid was decanted off. The solid was rinsed twice with ether and dried on a vacuum pump to give the title compound as a white solid (229 mg, 80.5%). 1H NMR (poor resolution in spectra) (400 MHz, METHANOL-d4) δ ppm 1.55-1.63 (m, 2 H) 1.69-1.73 (m, 3 H) 1.87-1.97 (m, 3 H) 2.11 (t, J=6.83 Hz, 0 H) 2.36-2.50 (m, 3 H) 2.61-2.72 (m, 1 H) 3.08-3.11 (m, 3 H) 3.99-4.10 (m, 4 H) 4.32-4.42 (m, 1 H) 6.89-6.97 (m, 1 H) 7.00-7.07 (m, 3 H) 7.67-7.73 (m, 2 H) 7.87 (t, J=10.54 Hz, 1 H). LCMS 479.6 (M+1).

Workup

  1. customevaporated in vacuo
  2. customto give a yellow oil
  3. customto give a yellow precipitate
  4. stirringThis suspension was stirred overnight at room temperature
  5. customthe liquid was decanted off
  6. washThe solid was rinsed twice with ether
  7. customdried on a vacuum pump

Sources & evidence

ORD record
ord-69c7dc2761834e6ea51793d29fb03221
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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