Diisopropylethylamine → HCID 46843294, compound

HRID 533740Notes

Reaction equation

HRID 533740 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:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30])#[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:29]([C:28]4[CH:27]=[C:26]([CH:34]=[CH:33][CH:32]=4)[C:24]#[N:25])=[O:30])[CH2:9][C:8]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 10953452Ether hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843294HCID 46843294, compoundYield 55.8%

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). 3-Cyanobenzoyl chloride (48 mg, 0.29 mmol) was added dropwise, and the reaction solution was allowed to stir 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 23 (25 mg, 28% 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-d7ae2bfc58064337bd98232468b6c176
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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