3-Buten-1-amine → HCID 68518948, compound

HRID 639910Notes

Reaction equation

HRID 639910 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:4]([C:21]#[N:22])[N:3]=1.[NH2:23][CH2:24][CH2:25][CH:26]=[CH2:27]>C(O)(C)C>[CH2:24]([NH:23][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:4]([C:21]#[N:22])[N:3]=1)[CH2:25][CH:26]=[CH2:27]

Participants

4

Reactant 2

HCID 4437323-Buten-1-amineHCID 112438971-Chloro-4-(3-fluorophenyl)-6-methoxyisoquinoline-3-carbonitrile

Product 1

HCID 68518948HCID 68518948, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 1-chloro-4-(3-fluorophenyl)-6-methoxyisoquinoline-3-carbonitrile (150 mg) in 15 mL isopropanol was added to 6 mL of a 0.81 M solution of 4-amino-1-butene. The mixture was heated to reflux for 4 days, then cooled to room temp and partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic solutions were washed with brine (1×), dried over MgSO4, and concentrated. Flash chromatography (3% to 50% EtOAc in hexanes) provided 146 mg of 1-(but-3-enylamino)-4-(3-fluorophenyl)-6-methoxyisoquinoline-3-carbonitrile as a tan solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 days
  3. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  4. washThe organic solutions were washed with brine (1×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eef6962d72704906a30ee7ffd905419a
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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