Azane;hydrate → HCID 57908193, compound

HRID 1044017Notes

Reaction equation

HRID 1044017 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH:11]3[CH2:14][CH2:13][CH2:12]3)[NH:8][C:5]2=[CH:6][N:7]=1.[NH3:15].O>CCO>[CH:11]1([C:9]2[NH:8][C:5]3=[CH:6][N:7]=[C:2]([NH2:15])[CH:3]=[C:4]3[CH:10]=2)[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 57908153HCID 57908153, compound

Product 1

HCID 57908193HCID 57908193, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

To the solution of 5-chloro-2-cyclobutyl-1H-pyrrolo[2,3-c]pyridine (200 mg, 0.97 mmol) in EtOH (10 mL) and NH3.H2O (30 mL) was added CuSO4.5H2O (30 mg, 0.12 mmol). The reaction mixture was stirred under 3 MPa at 180° C. for 16 h. The mixture was extracted with ethyl acetate (3×30 mL). The extract was dried, concentrated in vacuo and purified by chromatography on silica gel (5-10% MeOH in ethyl acetate as eluant) to afford the pure 2-cyclobutyl-1H-pyrrolo[2,3-c]pyridin-5-amine (40 mg, 22% yield). 1H NMR (300 MHz, MeOH) δ: 8.02 (s, 1H), 6.72 (s, 1H), 6.11 (s 1H), 3.72-3.60 (m, 1H), 2.47-1.90 (m, 6H). MS (ESI): m/z [M+H+] 188.1.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  2. customThe extract was dried
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography on silica gel (5-10% MeOH in ethyl acetate as eluant)

Sources & evidence

ORD record
ord-a4ba8916a28c4ae09739af577f1cc909
Source dataset
uspto-grants-2013_10
Patent number
US08563573B2

Reaction notes

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