1,4-Dioxane → HCID 178440827, compound

HRID 132110Notes

Reaction equation

HRID 132110 reaction equation
C(OC(=O)[NH:7][C:8]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:18]=2)[CH2:16][CH2:15][C:14]2[C:10](=[CH:11][NH:12][N:13]=2)[CH2:9]1)(C)(C)C.O1CCOCC1>Cl>[C:23]([C:19]1[CH:18]=[C:17]([C:8]2([NH2:7])[CH2:16][CH2:15][C:14]3[C:10](=[CH:11][NH:12][N:13]=3)[CH2:9]2)[CH:22]=[CH:21][CH:20]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 178452607HCID 178452607, compound

Product 1

HCID 178440827HCID 178440827, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

[5-(3-tert-Butyl-phenyl)-4,5,6,7-tetrahydro-2H-indazol-5-yl]-carbamic acid tert-butyl ester (84 mg, 0.23 mmol) was dissolved in 4 N hydrogen chloride in dioxane (2 mL, 8 mmol) at room temperatrure for 90 min, whereupon the reaction was deemed complete by TLC. The reaction mixture was concentrated under reduced pressure and the amine hydrochloride salt was basified by partitioning between 1 N aqueous NaOH and 33% isopropanol in chloroform. The organic layer was separated and the aqueous layer extracted twice with additional 33% IPA/CHCl3. The combined organic layers were dried (Na2SO4), filtered and concentrated. LC/MS analysis showed 90% pure material, which was taken to subsequent reactions: Rf=0.098 in 25% MeOH/CH2Cl2; retention time=0.98 min, method [7]; mass spec (ESI) 270 (6), 254 (23), 253 (100), 197 (12).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customby partitioning between 1 N aqueous NaOH and 33% isopropanol in chloroform
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted twice with additional 33% IPA/CHCl3
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-789f0fc9f530450dbd4ce118c9f990fd
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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