HCID 54332376, compound → HCID 18376126, compound

HRID 2300422Notes

Reaction equation

HRID 2300422 reaction equation
C([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][CH2:14][CH2:15][N:16]([S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:36])(=[O:29])=[O:28])[CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)=[CH:11][CH:12]=1)=[O:7])(C)(C)C>Cl.O1CCOCC1>[Cl:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[S:27]([N:16]([CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)[CH2:15][CH2:14][CH2:13][C:10]1[S:9][C:8]([C:6]([OH:7])=[O:5])=[CH:12][CH:11]=1)(=[O:28])=[O:29]

Participants

4

Reactant 1

HCID 54332376HCID 54332376, compound

Product 1

HCID 18376126HCID 18376126, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-(3-((2-chloro-benzenesulfonyl)-(3-(3-chloro-phenyl)-propyl)-amino)-propyl)-thiophene-2-carboxylic acid tert-butyl ester prepared of Example 6, Step A (0.010 g, 0.010 mmol) in 4N HCl in 1,4 dioxane (3 mL) and the reaction was stirred overnight at room temperature. HCl (g) was bubbled in until reaction was determined to be complete by thin layer chromatography. The reaction mixture was concentrated in vacuo. The resulting organic residue was azeotroped with CCl4 to produce a powder (5 mg). 1H NMR (400 MHz, CDCl3) δ 8.00 (d, 1H, J=4), 7.00-7.72 (m, 8H), 6.75 (d, 1H, J=4), 3.20-3.40 (m, 4H), 2.81 (m, 2H), 2.52 (m, 2H), 1.90 (m, 2H), 1.80 (m, 2H), 1.20 (m, 2H); MS 509.9 (M−1).

Workup

  1. customHCl (g) was bubbled in until reaction
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe resulting organic residue was azeotroped with CCl4

Sources & evidence

ORD record
ord-8c4404f4d27245949480e82d99e11b76
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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