Hydrochloric Acid → HCID 86671927, compound

HRID 84243Notes

Reaction equation

HRID 84243 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][C@@:19]([CH3:34])([S:30]([CH3:33])(=[O:32])=[O:31])[C:20]([NH:22][O:23]C4CCCCO4)=[O:21])[C:13](=[O:35])[CH:12]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Cl.O>ClCCl.O1CCOCC1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][C@@:19]([CH3:34])([S:30]([CH3:33])(=[O:31])=[O:32])[C:20]([NH:22][OH:23])=[O:21])[C:13](=[O:35])[CH:12]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86671928HCID 86671928, compound

Product 1

HCID 86671927HCID 86671927, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(2R)-4-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (581 mg, 1 mmol) was dissolved in 3 mL of dichloromethane. To this solution was added 1 mL of 4M HCl in dioxane 1 mL of water. The reaction was monitored for completion by LCMS. After standing overnight, a solid precipitated. The solid was collected by filteration and dried in vacuo yielding 25 mg (68%) of light yellow solid. LCMS m/z 423.5 (M+1) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3 H) 2.09-2.22 (m, 1 H) 2.36-2.46 (m, 1 H) 3.10 (s, 3 H) 3.65-3.79 (m, 1 H) 4.03-4.15 (m, 1 H) 4.28 (s, 4 H) 6.59-6.66 (m, 2 H) 6.94 (d, J=8.20 Hz, 1 H) 7.19-7.26 (m, 2 H) 7.67-7.73 (m, 1 H)

Workup

  1. customa solid precipitated
  2. customThe solid was collected by filteration
  3. customdried in vacuo
  4. customyielding 25 mg (68%) of light yellow solid

Sources & evidence

ORD record
ord-83384eb8ff034d5983a958571f80b7f2
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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