Cyclopropanecarboxaldehyde → HCID 67276277, compound

HRID 1894310Notes

Reaction equation

HRID 1894310 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-958353426b55485b881bf594c0dd4b85
Source dataset
uspto-grants-2013_08
Patent number
US08513283B2

Reaction notes

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