Pyrrolidine → HCID 58767540, compound

HRID 639934Notes

Reaction equation

HRID 639934 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([N:14]2[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]2)=[N:4][C:3]=1[C:20]#[N:21].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)(C)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5]([N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1)=[N:4][C:3]([C:20]#[N:21])=[C:2]2[N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 68518318HCID 68518318, compound

Product 1

HCID 58767540HCID 58767540, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
160 °C

Procedure

4-chloro-6-methoxy-1-(4-methyl-1H-imidazol-1-yl)isoquinoline-3-carbonitrile (0.010 g, 0.033 mmol) and pyrrolidine (0.048 g, 0.067 mmol) were combined in isopropanol (1 mL) in a sealed tube and heated at 160° C. in a microwave reactor for 1.5 h. Cooled to rt and partitioned between aqueous saturated NaHCO3 and EtOAc. The organic layer was washed with brine (1×), dried over Na2SO4 and concentrated. Purified by r.p. HPLC. The titled compound was obtained as a tan solid (free base, 0.0065 g, 58%). 1H NMR (500 MHz, CDCl3): δ 7.95 (d, J=9.0 Hz, 1H), 7.91 (s, 1H), 7.55 (d, J=2.7 Hz, 1H), 7.36 (dd, J=9.3, 2.7 Hz, 1H), 7.18(s, 1 H), 4.00 (s, 3H), 3.71-3.69 (m, 4H), 2.19-2.14 (m, 4H). HRMS 334.1666 (M+H)+.

Workup

  1. temperatureCooled to rt
  2. custompartitioned between aqueous saturated NaHCO3 and EtOAc
  3. washThe organic layer was washed with brine (1×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurified by r.p

Sources & evidence

ORD record
ord-2808e4ac91e940de996859562b047fa5
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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