1-Hydroxybenzotriazole → HCID 178423684, compound

HRID 1169420Notes

Reaction equation

HRID 1169420 reaction equation
[CH3:1][C:2]1[C:11]([C:12](O)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[CH:8]=2)[N:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[CH3:46][N:47]([CH2:54][C@H:55]1[CH2:60][CH2:59][C@H:58]([NH2:61])[CH2:57][CH2:56]1)[CH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1.C1CCN2C(=NCCC2)CC1>C(#N)C.C(N(CC)CC)C>[CH3:1][C:2]1[C:11]([C:12]([NH:61][C@H:58]2[CH2:57][CH2:56][C@H:55]([CH2:54][N:47]([CH3:46])[CH:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)[CH2:60][CH2:59]2)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)[CH:8]=2)[N:3]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 229902036-(4-Methylphenyl)-2-methylquinoline-3-carboxylic acidHCID 178484107HCID 178484107, compound

Product 1

HCID 178423684HCID 178423684, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

Into a suspension of 2-methyl-6-(4-methylphenyl)-quinoline-3-carboxylic acid (150 mg) and 1-hydroxybenzotriazole (109 mg) in acetonitrile (15 ml) was added at room temperature 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (156 mg), and the resulting mixture was stirred for 2 hours. Into the reaction mixture was added a solution of trans-4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]cyclohexylamine dihydrochloride (242 mg), 1,8-diazabicyclo[5,4,0]-7-undecene (246 mg) and triethylamine (0.15 ml) in acetonitrile (15 ml), and the resulting mixture was stirred for 4 days. After the reaction mixture was concentrated under reduced pressure, water was added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After the resulting organic layer was concentrated under reduced pressure to remove the solvent, the residue was subjected to purification using column chromatography (ethanol/ethyl acetate 1:2→1:1) and to recrystallization (ethyl acetate/hexane) to obtain trans-2-methyl-6-(4-methylphenyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]cyclohexyl]quinoline-3-carboxamide (compound 70) (142 mg) as colorless crystals.

Workup

  1. stirringthe resulting mixture was stirred for 4 days
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialwas dried with magnesium sulfate
  7. concentrationAfter the resulting organic layer was concentrated under reduced pressure
  8. customto remove the solvent
  9. customthe residue was subjected to purification
  10. customto recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e65f137b6dfd4016a117ea33dbff981b
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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