Sodium Hydroxide → HCID 45487130, compound

HRID 2354902Notes

Reaction equation

HRID 2354902 reaction equation
[OH-].[Na+].C([N:6]1[C:16]2[CH2:15][CH:14]3[N:17]([S:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[CH:10]([CH2:11][N:12]([C:28](=[O:30])[CH3:29])[CH2:13]3)[C:9]=2[CH:8]=[N:7]1)(=O)C>C1COCC1.C(OCC)(=O)C.O>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([S:18]([N:17]2[CH:14]3[CH2:13][N:12]([C:28](=[O:30])[CH3:29])[CH2:11][CH:10]2[C:9]2[CH:8]=[N:7][NH:6][C:16]=2[CH2:15]3)(=[O:19])=[O:20])=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59679481HCID 59679481, compound

Product 1

HCID 45487130HCID 45487130, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Aqueous sodium hydroxide (3 N, 0.56 mL, 1.70 mmol) was added to a stirring solution of 1-[5-acetyl-12-(4-chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-dien-10-yl]-ethanone (240 mg, 0.567 mmol) in THF (2 mL). The reaction mixture was stirred for 3 h at room temperature and subsequently diluted with ethyl acetate (10 mL) and water (5 mL). The phases were separated and the aqueous layer was extracted with ethyl acetate (2×5 mL). The organic extracts were combined, dried (Na2SO4), filtered, concentrated and purified by preparative HPLC to give 1-[12-(4-chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-dien-10-yl]-ethanone as a white solid. Retention time (min)=1.242, method [1], MS (ESI) 381.0 (M+H); 1H NMR (300 MHz, CDCl3) (rotamers) δ 7.68-7.58 (m, 2H), 7.44 and 7.41 (2×s, 1H), 7.38-7.30 (m, 2H), 5.32-5.20 (m, 1H), 4.78 and 4.55 (2×d, J=13.2 Hz, 1H), 4.48-4.35 (m, 1H), 3.90-3.54 (m, 2H), 3.08-2.62 (m, 3H), 2.00 and 1.61 (2×s, 3H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-aecb99b1af1e4d62aa3f5de392b59ba1
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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