Dichloromethane → N-(4-(1-hydroxycyclohexyl)benzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961442Notes

Reaction equation

HRID 1961442 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2([OH:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[CH:31][CH:30]=1.C(Cl)Cl>CCOC(C)=O>[OH:41][C:35]1([C:32]2[CH:31]=[CH:30][C:29]([CH2:28][NH:27][C:12]([C:11]3[C:2]([CH3:1])=[N:3][C:4]4[C:9]([CH:10]=3)=[CH:8][CH:7]=[CH:6][N:5]=4)=[O:14])=[CH:34][CH:33]=2)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 27369082-methyl-1,8-naphthyridine-3-carboxylic acidHCID 666332311-(4-(Aminomethyl)phenyl)cyclohexanol

Product 1

HCID 46908389N-(4-(1-hydroxycyclohexyl)benzyl)-2-methyl-1,8-naphthyridine-3-carboxamideYield 17.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

144 mg (0.76 mmol) 2-methyl-1,8-naphthyridine-3-carboxylic acid and 136 mg (0.84 mmol) CDI were refluxed in 5 ml EtOAc for 2 h. The solution was cooled to r.t. and 157 mg (0.76 mmol) 1-(4-(aminomethyl)phenyl)cyclohexanol followed by 5 ml CH2Cl2 was added. The mixture was stirred for 2 days at r.t. Concentrated to dryness and purified by flash chromatography (SiO2, CH2Cl2/MeOH 20:1→10:1) to afford 50 mg (13%) of the title compound.

Workup

  1. additionwas added
  2. concentrationConcentrated to dryness
  3. custompurified by flash chromatography (SiO2, CH2Cl2/MeOH 20:1→10:1)

Sources & evidence

ORD record
ord-0f45341a03c241dd946181785bb94778
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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