1-Hydroxybenzotriazole → HCID 19815989, compound

HRID 2247876Notes

Reaction equation

HRID 2247876 reaction equation
[C:1]([C:4]1[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)=[CH:6][C:7]([C:11]([OH:13])=O)=[N:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[O:45]1[CH2:50][CH2:49][N:48]([CH2:51][CH2:52][NH2:53])[CH2:47][CH2:46]1>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([C:4]1[C:9]([CH3:10])=[N:8][C:7]([C:11](=[O:13])[NH:53][CH2:52][CH2:51][N:48]2[CH2:49][CH2:50][O:45][CH2:46][CH2:47]2)=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19815943HCID 19815943, compound

Product 1

HCID 19815989HCID 19815989, compoundYield 34.6%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-acetyl-6-methyl-4-(3-nitrophenyl)-2-pyridinecarboxylic acid (0.95 g) in tetrahydrofuran (10 ml) was added N-hydroxybenzotriazole (0.43 g) and N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.61 g) at 5° C. After the mixture was stirred at the same temperature for 1 hour, 2-morpholinoethylamine (0.41 g) and triethylamine (0.32 g) was added thereto. The mixture was stirred at ambient temperature for 2 hours and diluted with ice-cold water (20 ml) and ethyl acetate (20 ml). The separated organic layer was washed with brine, dried and concentrated in vacuo. The residue was triturated with diethyl ether to give 3-acetyl-2-methyl-6-(2-morpholinoethylcarbamoyl)-4-(3-nitrophenyl)pyridine (0.45 g).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. washThe separated organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-bbada96bb1cf46caba1fc0f8fb4e58e5
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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