Diisopropylethylamine → HCID 46843366, compound

HRID 533745Notes

Reaction equation

HRID 533745 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:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1)#[N:25].Cl.CCOCC>C(Cl)Cl.CCOCC>[ClH:1].[C:24]([C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:33]([N:10]2[CH2:11][CH2:12][C:7]3[NH:6][C:5]4[N:13]=[CH:14][C:2]([Cl:1])=[CH:3][C:4]=4[C:8]=3[CH2:9]2)=[O:34])=[CH:30][CH:31]=1)#[N:25]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1703804-Cyanophenyl isocyanateHCID 10953452Ether hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843366HCID 46843366, compoundYield 128.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (50 mg, 0.24 mmol), and DIEA (0.04 mL, 0.24 mmol) were dissolved in DCM (2 mL). 4-Cyanophenyl isocyanate (34 mg, 0.24 mmol) was added and the reaction mixture was stirred overnight at room temperature. 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. Additional ether was added to drive precipitate formation. The resulting precipitate was filtered and dried under vacuum to provide 28 (60 mg, 64% yield) as a yellow solid. LC-MS (M+H=353, obsd.=353).

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-7a4d365ca3a14441abbcd20c2bf9b5f3
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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