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 2385897Notes

Reaction equation

HRID 2385897 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]

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 887MethanolSolvent

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 (2 H, s), 8.26 (1 H, d, J=8.20 Hz), 8.05 (1 H, s), 7.03 (1 H, dd, J=8.26, 1.83 Hz), 6.87 (1 H, d, J=1.78 Hz), 5.81-5.71 (1 H, m), 4.31 (2 H, t, J=5.01 Hz), 3.37 (2 H, t, J=5.01 Hz), 3.30 (2 H, d, J=12.46 Hz), 2.93 (2 H, d, J=11.52 Hz), 2.84-2.75 (1 H, m), 1.92-1.75 (4 H, m), 1.49 (6 H, 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-87dca17848eb49ab99dd1bf53aa19a54
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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