1,4-Dioxane hydrochloride → HCID 86271860, compound

HRID 2277069Notes

Reaction equation

HRID 2277069 reaction equation
Cl.O1CCOCC1.[O:8]=[S:9]1(=[O:37])[CH2:14][CH2:13][CH:12]([CH2:15][S:16]([C:19]2[CH:20]=[C:21]([C:25](=[O:36])[CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)[CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH2:11][CH2:10]1>C(Cl)Cl>[NH2:28][CH2:27][CH2:26][C:25]([C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([S:16]([CH2:15][CH:12]2[CH2:11][CH2:10][S:9](=[O:37])(=[O:8])[CH2:14][CH2:13]2)(=[O:17])=[O:18])[CH:20]=1)=[O:36]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 131733445HCID 131733445, compound

Product 1

HCID 86271860HCID 86271860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl/dioxane (4N, 5 mL) was added at 0° C. to a solution of tert-butyl (3-(3-(((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl)sulfonyl)phenyl)-3-oxopropyl)carbamate (0.40 g, 0.87 mmol) in CH2Cl2 (10 mL) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure to give after purification by preparative HPLC Example 24 as a white solid. Yield (200 mg, 50%); 1H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.31 (d, J=7.6 Hz, 1H), 8.20 (d, J=7.6 Hz, 1H), 7.88 (m, 4H), 3.56-3.52 (m, 2H), 3.50-3.47 (m, 2H), 3.20-3.17 (m, 4H), 3.05-3.02 (m, 2H), 2.31 (bs, 1H), 2.17-2.14 (m, 2H), 1.85-1.77 (m, 2H); MS: m/z 360.18 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give
  3. customafter purification by preparative HPLC Example 24 as a white solid
  4. customYield (200 mg, 50%)

Sources & evidence

ORD record
ord-ac4cc71e5307449cb5064c804f4dc9e5
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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