Cyclopropanecarboxaldehyde → HCID 67276277, compound

HRID 1697869Notes

Reaction equation

HRID 1697869 reaction equation
[NH2:1][C:2]1([CH2:5][O:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([O:17][C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[C:24]([C:28]([NH:30][CH3:31])=[O:29])=[CH:23][CH:22]=[CH:21]5)=[CH:12][CH:13]=[N:14]3)=[CH:9][C:8]=2[O:32][CH3:33])[CH2:4][CH2:3]1.[CH:34]1([CH:37]=O)[CH2:36][CH2:35]1.[BH4-].[Na+]>CCO>[CH:34]1([CH2:37][NH:1][C:2]2([CH2:5][O:6][C:7]3[CH:16]=[C:15]4[C:10]([C:11]([O:17][C:18]5[CH:19]=[C:20]6[C:25](=[CH:26][CH:27]=5)[C:24]([C:28]([NH:30][CH3:31])=[O:29])=[CH:23][CH:22]=[CH:21]6)=[CH:12][CH:13]=[N:14]4)=[CH:9][C:8]=3[O:32][CH3:33])[CH2:3][CH2:4]2)[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 4311764Sodium borohydrideHCID 25031915Lucitanib

Product 1

HCID 67276277HCID 67276277, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of Example 3 (100 mg) was refluxed with cyclopropanecarbaldehyde (2 eq) in EtOH (8 ml) for 4 hours. To the reaction was added NaBH4 (2.2 eq), the reaction was refluxed for 20 minutes and evaporated. The residue was purified with silica gel column to give the titled product (40 mg). Mass: (M+1), 498

Workup

  1. temperaturethe reaction was refluxed for 20 minutes
  2. customevaporated
  3. customThe residue was purified with silica gel column

Sources & evidence

ORD record
ord-2d08545bcc6f46c49420f52c35463427
Source dataset
uspto-grants-2012_04
Patent number
US08163923B2

Reaction notes

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