Hydrochloric Acid → 2-{4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-piperidin-1-yl}-ethanol

HRID 1849435Notes

Reaction equation

HRID 1849435 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]5[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][O:31]C6CCCCO6)[CH2:25][CH2:24]5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].Cl>CO>[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]5[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][OH:31])[CH2:25][CH2:24]5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58203894HCID 58203894, compound

Product 1

HCID 582042302-{4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-piperidin-1-yl}-ethanolYield 154.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-piperidin-4-yl}-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (103 mg, 0.20 mmol) in MeOH (2 mL) was added HCl (1 mL, 4N in dioxan) and the reaction mixture stirred at RT for 30 min. The reaction mixture was concentrated in vacuo and the residue freeze dried from MeOH/H2O to give 512 as a solid (136 mg). LCMS: RT=3.16 min, [M+H]+=440 [ad823338] 1H NMR 400 MHz (d6-DMSO) δ: 8.27 (1 H, d, J=8.19 Hz), 8.03 (1 H, s), 7.04 (1 H, dd, J=8.13, 1.84 Hz), 6.89 (1 H, d, J=1.75 Hz), 5.79-5.71 (1 H, m), 4.31 (2 H, t, J=5.0 Hz), 3.74 (2 H, t, J=5.0 Hz), 3.57 (2 H, d, J=12.01 Hz), 3.37 (2 H, t, J=4.96 Hz), 3.08-3.07 (4 H, m), 2.79 (1 H, t, J=7.80 Hz), 1.98-1.97 (4 H, m), 1.49 (6 H, d, J=6.59 Hz)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dry with materialthe residue freeze dried from MeOH/H2O

Sources & evidence

ORD record
ord-dabcc125fd7c4e77ba689d99a7734954
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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