Hydrogen chloride-ethyl acetate → Hydrochloric Acid

HRID 2385870Notes

Reaction equation

HRID 2385870 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]3[O:26][CH2:25][CH2:24][C:23]4[CH:22]=[C:21]([C:27]5[N:28]([C:32]6[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=6[F:39])[N:29]=[CH:30][N:31]=5)[S:20][C:19]=4[C:18]=3[N:40]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(C)=O)C.[ClH:47]>CCOC(C)=O>[F:39][C:33]1[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=1[N:28]1[C:27]([C:21]2[S:20][C:19]3[C:18]4[N:40]=[C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)[CH:15]=[CH:16][C:17]=4[O:26][CH2:25][CH2:24][C:23]=3[CH:22]=2)=[N:31][CH:30]=[N:29]1.[ClH:47]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 582038704-{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-yl}-piperazine-1-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidYield 77%HCID 579005292-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-9-piperazin-1-yl-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-{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-yl}-piperazine-1-carboxylic acid tert-butyl ester (0.61 g, 1.08 mmol) was dissolved in EtOAc, and EtOAc—HCl was added dropwise into the solution. And them the mixture was stirred at room temperature for 2 h. The reaction mixture was filtered to gather the solid. The resulting solid was washed by DCM (10 mL) to give 2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-9-piperazin-1-yl-4,5-dihydro-6-oxa-1-thia-10-aza-benzo[e]azulene as HCl salt (420 mg, yield: 77%). 1HNMR (D2O, 400 MHz): δ8.05 (s, 1H), 7.45-7.39 (m, 1H), 7.23 (t, J=8.8 Hz, 1H), 7.19 (t, J=8.4 Hz, 1H), 7.01 (s, 1H), 6.99 (d, J=1.6 Hz, 1H), 6.99 (d, J=4.8 Hz, 1H), 3.97 (s, 1H), 3.39 (s, 4H), 3.19 (s, 4H), 2.83 (s, 2H) ESI-MS: m/z=503 [M+H+]

Workup

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

Sources & evidence

ORD record
ord-30d4cb3d992e40af9fad9e38054027ef
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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