1,4-Dioxane hydrochloride → Hydrochloric Acid

HRID 1190650Notes

Reaction equation

HRID 1190650 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][NH:8][C:9]1[CH:10]=[CH:11][C:12]2[O:21][CH2:20][CH2:19][C:18]3[CH:17]=[C:16]([C:22]4[N:23]([C:27]5[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=5[F:34])[N:24]=[CH:25][N:26]=4)[S:15][C:14]=3[C:13]=2[N:35]=1)(C)(C)C.[ClH:37].O1CCOCC1>>[F:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]=1[N:23]1[C:22]([C:16]2[S:15][C:14]3[C:13]4[N:35]=[C:9]([NH:8][CH2:7][C:6]([OH:36])=[O:5])[CH:10]=[CH:11][C:12]=4[O:21][CH2:20][CH2:19][C:18]=3[CH:17]=2)=[N:26][CH:25]=[N:24]1.[ClH:37]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58204078HCID 58204078, compound

Product 2

HCID 313Hydrochloric AcidYield 57%HCID 58204146HCID 58204146, compound

Procedure

{2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulen-9-ylamino}-acetic acid tert-butyl ester (900 mg, 1.76 mmol) was dissolved in dioxane-HCl (20 mL), and the reaction mixture was stirred at room temperature for 0.5 h. The reaction mixture was filtered to gather the solid. The resulting solid was washed by DCM (10 mL) to give 449 as HCl salt (500 mg, yield: 57%). 1H NMR (DMSO-d6, 400 MHz): δ8.27 (s, 1H), 7.82-7.90 (m, 1H), 7.63-7.69 (m, 1H), 7.61-7.62 (m, 2H), 7.35-7.40 (m, 2H), 7.21 (s, 1H), 6.95 (s, 2H), 6.52 (d, J=8.8 Hz, 1H), 4.15 (t, J=4.0 Hz, 2H), 3.88 (s, 2H), 3.05 (t, J=4.8 Hz, 2H). LC-MS (ESI): m/z=456 [M+H]+

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe resulting solid was washed by DCM (10 mL)

Sources & evidence

ORD record
ord-3e3f38c1f59b4fa1857d7e3672a83ff9
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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