1,4-Dioxane hydrochloride → Hydrochloric Acid

HRID 1849370Notes

Reaction equation

HRID 1849370 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-8e0f5f2ce50e49f0859d694ed850d7ee
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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