1,4-Dioxane hydrochloride → HCID 135681563, compound

HRID 1793740Notes

Reaction equation

HRID 1793740 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:42]=[C:41]([CH3:43])[C:19]3[N:20]=[C:21]([C:23]4[C:24](=[O:40])[NH:25][CH:26]=[CH:27][C:28]=4[NH:29][CH2:30][CH:31]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=4)[OH:32])[NH:22][C:18]=3[CH:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.O1CCOCC1.Cl>CO>[Cl:39][C:35]1[CH:34]=[C:33]([CH:31]([OH:32])[CH2:30][NH:29][C:28]2[CH:27]=[CH:26][NH:25][C:24](=[O:40])[C:23]=2[C:21]2[NH:22][C:18]3[CH:17]=[C:16]([C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[O:15])[CH:42]=[C:41]([CH3:43])[C:19]=3[N:20]=2)[CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 135553465HCID 135553465, compound

Product 1

HCID 135681563HCID 135681563, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (±)-4-[1-(2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7-methyl-3H-benzimidazol-5-yl)-methanoyl]-piperazine-1-carboxylic acid tert-butyl ester (40 mg, 0.06 mmol) in methanol (5 mL) was added 4.0 M HCl dioxane solution (0.1 mL, excess). The reaction mixture was stirred at room temperature for 14 h. After concentration, the residue was purified by prep. HPLC to give the title compound (16 mg, 63%) as a white foam. 1H NMR (300 MHz, CD3OD) δ 7.56 (1H, s), 7.53 (1H, s), 7.23–7.41 (4H, m), 7.17 (1H, m), 6.26 (1H, d, J=7.6 Hz), 4.99 (1H, dd, J=4.7, 6.4 Hz), 3.91 (4H, broad s), 3.74 (1H, dd, J=4.7, 13.5 Hz), 3.65 (1H, dd, J=6.4, 13.5 Hz), 3.31 (4H, broad s), 2.63 (3H, s). LCMS (M+H)+ m/z 507 (t=1.38 min.).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-7e74e704a8844e3eaad4c028ece33304
Source dataset
uspto-grants-2006_07
Patent number
US07081454B2

Reaction notes

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