1,4-Dioxane → HCID 56941080, compound

HRID 714434Notes

Reaction equation

HRID 714434 reaction equation
[C:1]([NH:5][C:6](=[O:32])[CH:7]([C:19]1[C:27]2[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=2)[NH:21][C:20]=1[C:29]([OH:31])=[O:30])[N:8]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)C=O)([CH3:4])([CH3:3])[CH3:2].O1CCOCC1>O>[C:1]([NH:5][C:6](=[O:32])[CH:7]([C:19]1[C:27]2[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=2)[NH:21][C:20]=1[C:29]([OH:31])=[O:30])[NH:8][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 56846713HCID 56846713, compound

Product 1

HCID 56941080HCID 56941080, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 9l (24 mg, 0.05 mmol) was treated with 0.4 mL of dioxane (2M HCl), 0.1 mL of water stirring overnight under 60° C. After evaporation, the product was obtained as yellow solids (20 mg, yield: 89%). HPLC/MS: tR=10.42 min; m/z=448.3 [M+H]+ HRMS: C22H22Cl2N3O3, [M−H]−; 446.1038 (calcd.), 446.1050 (found). 1H NMR (600 MHz, MeOD, a mixture of rotamers): 1.25 (s, 9H), 1.31 (s, 6H), 4.27-4.33 (m, 2H), 4.70 (ABd, 1H, J=16.2 Hz), 5.13 (ABd, 1H, J=15.6 Hz), 5.88 (s, 1H), 6.24 (s, 1H), 6.47 (m, 1H), 6.76-7.27 (m, 8H), 7.39-7.60 (m, 6H), 7.79-7.85 (m, 2H), 8.38 (s, 1H), 8.47 (s, 1H), 11.35 (s, 1H), 11.60 (s, 1H). 13C NMR (150 MHz, MeOD, a mixture of rotamers): 27.3, 27.4, 46.5, 50.9, 51.0, 57.1, 111.6, 120.4, 121.3, 125.0, 126.8, 127.3, 127.5, 127.9, 128.6, 128.9, 129.0, 129.6, 131.0, 132.1, 135.3, 135.5, 170.1.

Workup

  1. customAfter evaporation

Sources & evidence

ORD record
ord-e3149da90a0244e6aba85e967b2e3110
Source dataset
uspto-grants-2015_11
Patent number
US09187441B2

Reaction notes

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