(Dicyclopropylmethyl)amine → 7-Chloro-1-[(dicyclopropylmethyl)amino]-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1970997Notes

Reaction equation

HRID 1970997 reaction equation
Cl[C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][C:10]([Cl:15])=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:16]#[N:17])=[CH:4][N:3]=1.[CH:18]1([CH:21]([CH:23]2[CH2:25][CH2:24]2)[NH2:22])[CH2:20][CH2:19]1>O1CCOCC1>[Cl:15][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[C:2]([NH:22][CH:21]([CH:23]4[CH2:25][CH2:24]4)[CH:18]4[CH2:20][CH2:19]4)=[N:3][CH:4]=[C:5]([C:16]#[N:17])[C:6]=3[NH:7][C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 83390(Dicyclopropylmethyl)amineHCID 565950571,7-dichloro-5H-pyrido[4,3-b]indole-4-carbonitrile

Product 1

HCID 565953247-Chloro-1-[(dicyclopropylmethyl)amino]-5H-pyrido[4,3-b]indole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
135 °C

Procedure

To a stirred slurry of 1,7-dichloro-5H-pyrido[4,3-b]indole-4-carbonitrile (16 g, 61 mmol) in dioxane (122 mL) was added dicyclopropylmethanamine (17 g, 153 mmol). The reaction mixture was heated to 135° C. for 1 d, cooled to room temperature, and concentrated. The residue was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc (×3). The combined organics were washed with brine, dried (sodium sulfate), concentrated, and purified by flash chromatography to give the title compound. LRMS (APCI) calc'd for (C19H17ClN4) [M+H]+, 337.1. found 337.1.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. additionThe residue was diluted with EtOAc and water
  4. extractionThe aqueous layer was extracted with EtOAc (×3)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-94dacf776b7440d6a4a635d0c69a5e02
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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