Dimethylamine → HCID 86615278, compound

HRID 1445137Notes

Reaction equation

HRID 1445137 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]=O.Cl.[CH2:7]([N:10]1[C:14]2=[C:15]([N:28]3[CH2:37][CH2:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29]3)[N:16]=[C:17]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[O:20])[CH:18]=[C:13]2[C:12]([CH2:38]C#N)=[C:11]1[CH3:41])[CH:8]=[CH2:9].[I:42]C>C(O)C.C(O)(=O)C>[I-:42].[CH2:7]([N:10]1[C:14]2=[C:15]([N:28]3[CH2:37][CH2:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29]3)[N:16]=[C:17]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[O:20])[CH:18]=[C:13]2[C:12]([CH2:38][N+:2]([CH3:4])([CH3:3])[CH3:1])=[C:11]1[CH3:41])[CH:8]=[CH2:9]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 6328Methyl iodideHCID 67142450HCID 67142450, compound

Product 1

HCID 86615278HCID 86615278, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

Dimethylamine (1.05 ml, 2.1 mmol), acetic acid (0.81 ml), and formaldehyde (442 μl) were added to a solution of 1-allyl-7-(3,4-dihydro-1H-isoquinolin-2-yl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl]-(4-methylpiperazin-1-yl)-methanone (600 mg, 1.40 mmol) prepared in Step 2 in ethanol (5 ml). The reaction mixture was refluxed overnight and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (methanol/dichloromethane=1/10, v/v). The resulting white solid (300 mg, 0.62 mmol) was dissolved in ethanol (2 ml) and then iodomethane (77.2 μl, 1.24 mmol) was added thereto. The reaction mixture was stirred overnight at room temperature and then filtered. The resulting residue was dried to give 100 mg of the titled compound as a white solid. The product was used in the subsequent step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (methanol/dichloromethane=1/10
  4. filtrationfiltered
  5. customThe resulting residue was dried

Sources & evidence

ORD record
ord-dd7ad16c62d947d1808b372d668a1cc4
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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