Hydrochloric Acid → HCID 22380175, compound

HRID 1988775Notes

Reaction equation

HRID 1988775 reaction equation
Cl.[CH2:2]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]#[C:14][CH2:15][CH:16]([OH:18])[CH3:17])=[CH:12][C:7]=2[N:6]=[C:5]1[CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[CH3:3].C([O-])(O)=[O:31].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].Cl[Pd]Cl.C(Cl)Cl>[CH2:2]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13](=[O:31])[CH2:14][CH2:15][CH:16]([OH:18])[CH3:17])=[CH:12][C:7]=2[N:6]=[C:5]1[CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22380052HCID 22380052, compound

Product 1

HCID 22380175HCID 22380175, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To the bi-layer system of 3 N HCl (5 mL) and CH2Cl2 is added 5-(1-ethyl-2-{[2-(1,3-thiazol-2-yl)-1H-imidazol-1-yl]methyl}-1H-benzimidazol-5-yl)-pent-4-yn-2-ol (107 mg, 0.27 mmol), PdCl2 (5 mg, 0.028 mmol), and n-Bu4NCl (17 mg, 0.056 mmol). The resulting mixture is stirred at room temperature for 72 hr, and then poured into saturated NaHCO3 solution. The aqueous layer is extracted with CH2Cl2 and the combined organic layers are dried over Na2SO4. Solvent is removed and purification by preparative TLC provides the product as white solid. 1H NMR (CDCl3) δ 8.44 (d, 1H), 7.80 (dd, 1H), 7.85 (d, 1H), 7.40 (d, 1H), 7.36 (d, 1H), 7.18 (d, 1H), 7.14 (d, 1H), 6.36 (s, 2H), 4.27 (q, 2H), 3.86 (m, 1H), 3.19 (t, 2H), 1.93 (m, 2H), 1.25 (d, 3H), 1.09 (t, 3H). LCMS 410.2 (MH+).

Workup

  1. extractionThe aqueous layer is extracted with CH2Cl2
  2. dry with materialthe combined organic layers are dried over Na2SO4
  3. customSolvent is removed
  4. custompurification by preparative TLC

Sources & evidence

ORD record
ord-8cab6cea8aeb46d58f346c0a1f1fa7c0
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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