1-Hydroxybenzotriazole → 1-(3-Formyl-4-nitrophenyl)-4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)piperazine

HRID 704629Notes

Reaction equation

HRID 704629 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=[C:4]2[CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.[CH:37]([C:39]1[CH:40]=[C:41]([N:48]2[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)[CH:42]=[CH:43][C:44]=1[N+:45]([O-:47])=[O:46])=[O:38]>C(N(CC)CC)C.CN(C)C=O>[CH:37]([C:39]1[CH:40]=[C:41]([N:48]2[CH2:53][CH2:52][N:51]([C:11]([C:9]3[N:10]=[C:4]4[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]4[CH:8]=3)=[O:13])[CH2:50][CH2:49]2)[CH:42]=[CH:43][C:44]=1[N+:45]([O-:47])=[O:46])=[O:38]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 10725557-Methylimidazo(1,2-a)pyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 132363002-Nitro-5-piperazinylbenzaldehyde hydrochloride

Product 1

HCID 200728461-(3-Formyl-4-nitrophenyl)-4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)piperazineYield 98.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 7-methylimidazo[1,2-a]pyridine-2-carboxylic acid (10.56 g), 1-hydroxybenzotriazole (8.1 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (11.46 g) and N,N-dimethylformamide (360 ml) was stirred for 1 hour at ambient temperature. 1-(3-Formyl-4-nitrophenyl)piperazine hydrochloride (16.2 g) and triethylamine (9.1 g) were added thereto and the mixture was stirred for 1 hour. The resulting precipitates were collected, washed with ethyl acetate (100 ml×2) and water (100 ml×2), and dried to give 1-(3-formyl-4-nitrophenyl)-4-(7-methylimidazo[1,2-a]pyridine-2-carbonyl)piperazine (23.0 g).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customThe resulting precipitates
  3. customwere collected
  4. washwashed with ethyl acetate (100 ml×2) and water (100 ml×2)
  5. customdried

Sources & evidence

ORD record
ord-141d341de14f4a02a3bfae002baaa49b
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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