Ether hydrochloride → cis-3-[(4-propoxy-1H-indazol-5-yl)oxy]cyclohexanamine hydrochloride

HRID 1269937Notes

Reaction equation

HRID 1269937 reaction equation
[ClH:1].C(OCC)C.[CH2:7]([O:10][C:11]1[C:19]([O:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][C@H:23]([NH2:27])[CH2:22]2)=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][NH:15]2)[CH2:8][CH3:9]>CO>[ClH:1].[CH2:7]([O:10][C:11]1[C:19]([O:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][C@H:23]([NH2:27])[CH2:22]2)=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][NH:15]2)[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 69432506cis-3-[(4-propoxy-1H-indazol-5-yl)oxy]cyclohexanamine

Product 1

HCID 69433087cis-3-[(4-propoxy-1H-indazol-5-yl)oxy]cyclohexanamine hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, 1M-hydrochloric acid-diethyl ether (341 μl, 0.341 mmol) was added dropwise to a solution of cis-3-[(4-propoxy-1H-indazol-5-yl)oxy]cyclohexanamine (82.3 mg, 0.284 mmol) in methanol (2 ml) at room temperature. After 1 hour, the mixture thus obtained was concentrated under reduced pressure and the resulting residue was crystallized from ethyl acetate, followed by filtration under reduced pressure, and then drying. The solid thus obtained was washed with hexane by repulping to obtain cis-3-[(4-propoxy-1H-indazol-5-yl)oxy]cyclohexanamine hydrochloride (76.8 mg, 83%).

Workup

  1. customthe mixture thus obtained
  2. concentrationwas concentrated under reduced pressure
  3. customthe resulting residue was crystallized from ethyl acetate
  4. filtrationfollowed by filtration under reduced pressure
  5. customdrying
  6. customThe solid thus obtained
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-8d7aa124532f48b88a2e8567996019fe
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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