Diisopropylethylamine → HCID 46843370, compound

HRID 533747Notes

Reaction equation

HRID 533747 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.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1.Cl.CCOCC>C(Cl)Cl.CCOCC>[ClH:1].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([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:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 878433-Methoxyphenyl isocyanateHCID 10953452Ether hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843370HCID 46843370, compoundYield 59.3%

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). 3-Methoxyphenyl isocyanate (0.03 mL, 0.24 mmol) was added dropwise, and the reaction solution 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 30 (28 mg, 30% yield) as a yellow solid. LC-MS (M+H=357, obsd.=357).

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-e256836e3b75434f96712166354480d6
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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