1,4-Dioxane → HCID 53259021, compound

HRID 1616867Notes

Reaction equation

HRID 1616867 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:20]=[CH:19][C:18]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)(=[O:23])=[O:22])=[CH:17][C:15]=3[O:16][C:10]=2[C:9]1([CH3:32])[CH3:31])=O)(C)(C)C.O1CCOCC1>Cl>[F:30][C:26]1[CH:25]=[C:24]([S:21]([C:18]2[CH:19]=[CH:20][C:14]3[C:11]4[CH2:12][CH2:13][NH:8][C:9]([CH3:32])([CH3:31])[C:10]=4[O:16][C:15]=3[CH:17]=2)(=[O:22])=[O:23])[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 67324687HCID 67324687, compound

Product 1

HCID 53259021HCID 53259021, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

7-(3-Fluoro-benzenesulfonyl)-1,1-dimethyl-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester (0.200 g, 0.435 mmol) in 4M HCl in dioxane (5.0 mL, 57.7 mmol) was stirred at rt. After 4 h, the heterogenous mixture was concentrated and triturated with Et2O. The resulting white precipitate was dried under vacuum at 80° C. for 15 h. mp 110-114° C.; MS m/z 360 [M+H]+. 1H-NMR (400 MHz, CDCl3): δ 1.7 (s, 6H), 3.0 (m, 2H), 3.5 (m, 2H), 7.5 (m, 1H), 7.7 (m, 1H), 7.9 (m, 4H), 8.3 (s, 1H), 10.0 (brs, 2H).

Workup

  1. concentrationthe heterogenous mixture was concentrated
  2. customtriturated with Et2O
  3. customThe resulting white precipitate was dried under vacuum at 80° C. for 15 h. mp 110-114° C.

Sources & evidence

ORD record
ord-158aa04ba4204af1b18bebcc38ffd379
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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