HCID 86593610, compound → HCID 178511698, compound

HRID 1269811Notes

Reaction equation

HRID 1269811 reaction equation
CN.C(CN)O.[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][C@@H:17]3[CH2:22][CH2:21][C@H:20]([N:23]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:19][CH2:18]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1>O>[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][C@@H:17]3[CH2:22][CH2:21][C@H:20]([NH2:23])[CH2:19][CH2:18]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 86593610HCID 86593610, compoundHCID 178515013HCID 178515013, compound

Product 1

HCID 178511698HCID 178511698, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 30%-methylamine-ethanolamine solution (1.0 ml) was added to the cis-2-[4-(1H-indazol-5-yloxy)cyclohexyl]-1H-isoindole-1,3(2H)-dione (100 mg, 0.277 mmol) obtained in Example 380. After 22 hours, the mixture thus obtained was poured into water (20 ml) and extracted with ethyl acetate (20 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol/(1%-aqueous ammonia)) to obtain cis-4-(1H-indazol-5-yloxy)cyclo-hexanamine (36 mg, 57%).

Workup

  1. customthe mixture thus obtained
  2. extractionextracted with ethyl acetate (20 ml×2)
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe organic layer dried
  5. concentrationwas concentrated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol/(1%-aqueous ammonia))

Sources & evidence

ORD record
ord-687999ba633c4001a2e569d04945d82a
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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