Cyclopropanemethanamine → HCID 57975970, compound

HRID 1865205Notes

Reaction equation

HRID 1865205 reaction equation
FC1C(O[C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[C:30]4[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=4)[N:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=3)=[O:10])=C(F)C(F)=C(F)C=1F.[CH:39]1([CH2:42][NH2:43])[CH2:41][CH2:40]1>C1COCC1>[CH:39]1([CH2:42][NH:43][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[C:30]4[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=4)[N:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=3)=[O:10])[CH2:41][CH2:40]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 86601399HCID 86601399, compound

Product 1

HCID 57975970HCID 57975970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(6,7-dimethoxy-quinolin-4-yloxy)-1H-indole-2-carboxylic acid pentafluorophenyl ester (0.5 g, above) in 5 mL of THF was added cyclopropylmethylamine (0.175 g, 2.46 mmol, Aldrich) and resulting solution was stirred at RT for 8 h. The mixture was concentrated in vacuo. The residue was diluted with 50 mL of EtOAc and washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (30% to 100% EtOAc/hexane) to afford white solid as desired product. MS (ESI pos. ion) m/z: 418 (M+H). Calc'd Exact Mass for C24H23N3O4: 417.46.

Workup

  1. customresulting solution
  2. concentrationThe mixture was concentrated in vacuo
  3. additionThe residue was diluted with 50 mL of EtOAc
  4. washwashed with 20 mL of satd
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by silica gel column chromatography (30% to 100% EtOAc/hexane)

Sources & evidence

ORD record
ord-e18e7c007ea2423ebc3a48cc36d2123e
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Reaction notes

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