Cyclopropanecarboxaldehyde → HCID 25017408, compound

HRID 1686052Notes

Reaction equation

HRID 1686052 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][C:26]4([NH2:29])[CH2:28][CH2:27]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:30])[NH:6]2.[CH:31]1([CH:34]=O)[CH2:33][CH2:32]1.[BH4-].[Na+]>CCO>[CH:31]1([CH2:34][NH:29][C:26]2([CH2:25][O:24][C:18]3[CH:17]=[C:16]4[C:21]([C:12]([O:11][C:10]5[C:2]([F:1])=[C:3]6[C:7](=[CH:8][CH:9]=5)[NH:6][C:5]([CH3:30])=[CH:4]6)=[CH:13][CH:14]=[N:15]4)=[CH:20][C:19]=3[O:22][CH3:23])[CH2:27][CH2:28]2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 4311764Sodium borohydrideHCID 25017411Anlotinib

Product 1

HCID 25017408HCID 25017408, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of Example 24 (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 (50 mg). Mass: (M+1), 462

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-075172a312df46d0b9831bcce6e784fd
Source dataset
uspto-grants-2012_04
Patent number
US08148532B2

Reaction notes

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