Triethylamine → HCID 67052399, compound

HRID 599433Notes

Reaction equation

HRID 599433 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:12](CC)CC)C.Cl.[Cl:18][CH2:19][C:20]1[N:21]([CH2:33][CH2:34][CH2:35]N)[C:22]2[C:31]3[N:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[CH:24][C:23]=2[N:32]=1>ClCCl>[Cl:18][CH2:19][C:20]1[N:21]([CH2:33][CH2:34][CH2:35][N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([NH2:12])=[O:9])[C:22]2[C:31]3[N:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[CH:24][C:23]=2[N:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 66958569HCID 66958569, compound

Product 1

HCID 67052399HCID 67052399, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclohexyl isocyanate (0.70 mL, 5.50 mmol) and triethylamine (1.74 mL, 12.5 mmol) were added to a stirred suspension of 3-[2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propan-1-amine hydrochloride (prepared as described in Parts A-E of Example 92, 1.56 g, 5.00 mmol) in dichloromethane (25 mL). A solution eventually formed from which a solid precipitated. The mixture was allowed to stand at room temperature overnight, then the solid was isolated by filtration and washed with a minimal amount of dichloromethane to afford 1.52 g of N-{3-[2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}-N-cyclohexylurea as a white solid.

Workup

  1. customA solution eventually formed from which a solid
  2. customprecipitated
  3. customthe solid was isolated by filtration
  4. washwashed with a minimal amount of dichloromethane

Sources & evidence

ORD record
ord-57dc7d8258134545a37a1c7e4eb63131
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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