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

HRID 1190581
Notes
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Reaction equation

HRID 1190581 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:35]=[CH:34][C:17]3[C:18]4[N:19]=[C:20]([C:26]5[N:27]([CH:31]([CH3:33])[CH3:32])[N:28]=[CH:29][N:30]=5)[S:21][C:22]=4[CH2:23][CH2:24][O:25][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[CH:31]([N:27]1[C:26]([C:20]2[S:21][C:22]3[CH2:23][CH2:24][O:25][C:16]4[CH:15]=[C:14]([CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[CH:35]=[CH:34][C:17]=4[C:18]=3[N:19]=2)=[N:30][CH:29]=[N:28]1)([CH3:33])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 582039364-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 582037792-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-piperidin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneYield 28%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

Alternatively, to a suspension of 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]-piperidine-1-carboxylic acid tert-butyl ester (470 mg, 0.95 mmol) in MeOH (10 mL) was added 1M HCl in ether (1.9 mL, 1.90 mmol). The reaction mixture was stirred for 18 hours then the volatiles were removed in vacuo. The resultant residue was stirred in diethyl ether (20 mL) for 20 minutes then the solid was filtered off and further triturated with a mixture of MeOH and ether to give 375 as a white solid (104 mg, 28%). LCMS: RT=7.82 min, [M+H]+=396. 1H NMR δ (ppm) (DMSO-d6): 8.86 (2H, s), 8.26 (1H, d, J=8.20 Hz), 8.05 (1H, s), 7.03 (1H, dd, J=8.26, 1.83 Hz), 6.87 (1H, d, J=1.78 Hz), 5.81-5.71 (1H, m), 4.31 (2H, t, J=5.01 Hz), 3.37 (2H, t, J=5.01 Hz), 3.30 (2H, d, J=12.46 Hz), 2.93 (2H, d, J=11.52 Hz), 2.84-2.75 (1H, m), 1.92-1.75 (4H, m), 1.49 (6H, d, J=6.59 Hz)

Workup

  1. customthe volatiles were removed in vacuo
  2. stirringThe resultant residue was stirred in diethyl ether (20 mL) for 20 minutes
  3. filtrationthe solid was filtered off
  4. customfurther triturated with a mixture of MeOH and ether

Sources & evidence

ORD record
ord-97f07559298a49c69f6d24624387779f
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673952B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes