Hydrochloric Acid → HCID 67050622, compound

HRID 707834Notes

Reaction equation

HRID 707834 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([C:12]2[CH:44]=[CH:43][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:40]([CH3:42])[CH3:41])[N:26]=[C:27]([NH:29][C:30]([O:32][CH2:33][C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=6)=[O:31])[N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1)=O)(C)(C)C.[ClH:45].CO>C(Cl)Cl.O1CCOCC1>[ClH:45].[CH2:33]([O:32][C:30](=[O:31])[NH:29][C:27]1[N:28]=[C:24]([C:18]2[S:19][C:20]3[CH2:21][CH2:22][O:23][C:14]4[CH:13]=[C:12]([CH:10]5[CH2:9][NH:8][CH2:11]5)[CH:44]=[CH:43][C:15]=4[C:16]=3[N:17]=2)[N:25]([CH:40]([CH3:41])[CH3:42])[N:26]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 58204252HCID 58204252, compound

Product 1

HCID 67050622HCID 67050622, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 3-[2-(5-benzyloxycarbonylamino-2-isopropyl-2H-[1,2,4]-triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester (504 mg, 0.82 mmol) in DCM (10 mL) was added 4N HCl in dioxan (2 mL) at RT. After stirring for 2 hours MeOH (2 mL) and 4N HCl in dioxan (3 mL) were added to the mixture. After stirring for 60 minutes the reaction mixture was concentrated in vacuo. The resulting solid was treated with ether, collected by filtration and dried under vacuum to afford [5-(8-azetidin-3-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-1-isopropyl-1H-[1,2,4]triazol-3-yl]-carbamic acid benzyl ester hydrochloride salt (379 mg, 84%). LCMS: RT=3.04 min, [M+H]+=517

Workup

  1. additionwere added to the mixture
  2. concentrationwas concentrated in vacuo
  3. additionThe resulting solid was treated with ether
  4. filtrationcollected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-cb49263e37fc4bca85ea8c3045709977
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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