1,4-Dioxane hydrochloride → HCID 69219529, compound

HRID 272714Notes

Reaction equation

HRID 272714 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:30][CH2:31][C@H:32]2[CH2:36][CH2:35][CH2:34][N:33]2C(OC(C)(C)C)=O)=[CH:5][C:6]2[NH:12][C:11]3[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH3:27])[CH:18]=4)[CH:15]=[CH:16][C:10]=3[C:9](=[O:28])[NH:8][C:7]=2[CH:29]=1.Cl.O1CCOCC1>CO>[CH3:1][O:2][C:3]1[C:4]([O:30][CH2:31][C@H:32]2[CH2:36][CH2:35][CH2:34][NH:33]2)=[CH:5][C:6]2[NH:12][C:11]3[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([O:26][CH3:27])[CH:18]=4)[CH:15]=[CH:16][C:10]=3[C:9](=[O:28])[NH:8][C:7]=2[CH:29]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 91123624HCID 91123624, compound

Product 1

HCID 69219529HCID 69219529, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 489B in methanol (2 mL) was treated with 4.0N HCl/dioxane (0.15 mL, 0.6 mmol), stirred overnight at room temperature, concentrated under vacuum, and purified by preparative HPLC to give 3.9 mg (9%) of the desired product as the TFA salt. MS (ESI) m/e 491 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 9.72 (s, 1H), 8.70 (s, 1H), 8.02 (d, J=8.1 Hz, 1H), 7.77-7.80 (m, 2H), 7.53 (d, J=1.4 Hz, 1H), 7.29-7.36 (m, 3H), 6.75 (s, 1H), 6.71 (s, 1H), 4.15 (m, 1H), 4.03 (s, 3H), 3.83-3.96 (m, 1H), 3.71 (s, 3H), 3.17-3.27 (m, 3H), 2.13 (m, 1H), 1.84-2.01 (m, 2H), 1.72 (m, 1H).

Workup

  1. concentrationconcentrated under vacuum
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d538e896ca374402ad9f157ff56a83c8
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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