Hydrochloric Acid → HCID 68313155, compound

HRID 1530386Notes

Reaction equation

HRID 1530386 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([CH:15]([O:17][C:18]2[CH:40]=[CH:39][C:21]3[C:22]4[N:26]([CH2:27][CH2:28][O:29][C:20]=3[CH:19]=2)[CH:25]=[C:24]([C:30]2[N:31]([CH:36]([CH3:38])[CH3:37])[N:32]=[C:33]([CH3:35])[N:34]=2)[N:23]=4)[CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:8]1[CH2:14][CH2:13][CH2:12][CH:11]([CH:15]([O:17][C:18]2[CH:40]=[CH:39][C:21]3[C:22]4[N:26]([CH2:27][CH2:28][O:29][C:20]=3[CH:19]=2)[CH:25]=[C:24]([C:30]2[N:31]([CH:36]([CH3:37])[CH3:38])[N:32]=[C:33]([CH3:35])[N:34]=2)[N:23]=4)[CH3:16])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68313148HCID 68313148, compound

Product 1

HCID 68313155HCID 68313155, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-{1-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]ethyl}azepane-1-carboxylic acid tertbutyl ester (60 mg, 0.11 mmol) in dioxane (1 mL) was added HCl (2.5M in MeOH, 1 mL) and the reaction mixture was stirred for 1 h at RT. Volatiles were then removed in vacuo and the resulting residue was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 0.5M NH3/MeOH affording 8-(1-Azepan-4-ylethoxy)-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (50 mg, quantitative). LCMS: RT 2.26 min [M+H]+ 451.2

Workup

  1. customVolatiles were then removed in vacuo
  2. washwas washed with MeOH
  3. washthe product eluted with 0.5M NH3/MeOH

Sources & evidence

ORD record
ord-45b36c29670e45068255da67af48696d
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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