1,4-Dioxane hydrochloride → HCID 44453209, compound

HRID 272710Notes

Reaction equation

HRID 272710 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:30]COCC[Si](C)(C)C)=[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>C(Cl)Cl.CO>[OH:30][C:4]1[C:3]([O:2][CH3:1])=[CH:29][C:7]2[NH:8][C:9](=[O:28])[C:10]3[CH:16]=[CH:15][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:13][C:11]=3[NH:12][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69219966HCID 69219966, compound

Product 1

HCID 44453209HCID 44453209, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 476H (429 mg, 0.8 mmol) in methylene chloride (20 mL) and methanol (10 mL) was treated with 4N HCl/dioxane (1 mL, 4.0 mmol) and stirred one hour at room temperature. The mixture was concentrated under vacuum to provide 325 mg (quantitative) of desired product. MS (ESI) m/e 408 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 9.57 (s, 1H), 8.89 (s, 1H), 8.01 (d, J=8.1 Hz, 1H), 7.76 (d, J=8.1 Hz, 1H), 7.65 (s, 1H), 7.51 (d, J=1.7 Hz, 1H), 7.26-7.35 (m, 3H), 6.59 (s, 1H), 6.52 (s, 1H), 4.03 (s, 3H), 3.67 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-f72a76a37a174afe8dd7a90080dc7883
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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