4-Cyanobenzoyl chloride → HCID 46843292, compound

HRID 533739Notes

Reaction equation

HRID 533739 reaction equation
[Cl:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]3[CH2:12][CH2:11][NH:10][CH2:9][C:8]=3[C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[C:24]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)#[N:25].Cl.CCOCC>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]3[CH2:12][CH2:11][N:10]([C:30]([C:29]4[CH:33]=[CH:34][C:26]([C:24]#[N:25])=[CH:27][CH:28]=4)=[O:31])[CH2:9][C:8]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 801724-Cyanobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 10953452Ether hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843292HCID 46843292, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (50 mg, 0.24 mmol) and DIEA (0.05 mL, 0.29 mmol) were dissolved in THF (2 mL). 4-Cyanobenzoyl chloride (47.84 mg; 0.29 mmol) was added dropwise, and the reaction mixture was stirred at room temperature for 1 h. The crude reaction mixture was concentrated, and converted to the HCl salt by dissolving the crude material in MeOH (2 ml) and adding 1 M HCl/ether (2 equiv). The resulting solution was refrigerated overnight. The resulting precipitate was filtered and dried under vacuum to provide 22 (40 mg, 45% yield) as a pale yellow solid. LC-MS (M+H=337, obsd.=337).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. dissolutionby dissolving the crude material in MeOH (2 ml)
  4. waitThe resulting solution was refrigerated overnight
  5. filtrationThe resulting precipitate was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b9ef23edadd24a959e06b6e8401bf952
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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