Hydrochloric Acid → Hydrochloric Acid

HRID 2240080Notes

Reaction equation

HRID 2240080 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([S:16]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[N:12][NH:13]2)=[CH:9][CH:8]=1)=[N+]=[N-].CO.[ClH:31].CCOCC>C1COCC1.[Pd].C(Cl)Cl.CCCCCC>[C:19]1([S:16]([C:11]2[C:10]3[C:14](=[CH:15][C:7]([O:6][CH2:5][CH2:4][NH2:1])=[CH:8][CH:9]=3)[NH:13][N:12]=2)(=[O:17])=[O:18])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.[ClH:31]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3283Diethyl EtherHCID 178514596HCID 178514596, compound

Product 2

HCID 313Hydrochloric AcidHCID 178511385HCID 178511385, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

A mixture of 6-(2-azido-ethoxy)-3-(naphthalene-1-sulfonyl)-1H-indazole (0.17 g, 0.45 mmoles) and 10% Pd/C in THF (2 mL), and methanol (8 mL) was hydrogenated in a Parr hydrogenation bottle (250 mL) at 52 lb/in2 for 2 hours. The mixture was filtered through Celite, and the filtrate was concentrated under vacuum. The crude product was recrystallized from CH2Cl2/hexane, 1M HCl in ether (0.4 mL, 0.4 mmoles) was added, then dried, to afford the title compound as an off-white HCl salt (0.15 g, 0.4 mmoles), MS: (ES+) 368 [M+H]+

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. additionwas added
  4. customdried

Sources & evidence

ORD record
ord-28292a93930c4e8b877705e91e19e9f0
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

Loading…