1,4-Dioxane hydrochloride → Hydrochloric Acid

HRID 2385964Notes

Reaction equation

HRID 2385964 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-653d8e64ba8543efb7b834cef8d3b2c0
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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