HCID 54332376, compound → HCID 18376126, compound

HRID 2117472Notes

Reaction equation

HRID 2117472 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-d1ff5fface7f41029d273818b7ec2df3
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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