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3,4-Dichlorobenzoic acid → Methyl (5-{4-[(3,4-dichloro-benzoyl)amino]benzyl}imidazo[1,2-c]pyrimidin-8-yl)acetate

HRID 2353325
Notes
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Reaction equation

HRID 2353325 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][C:9]2[N:14]3[CH:15]=[CH:16][N:17]=[C:13]3[C:12]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:11][N:10]=2)=[CH:6][CH:5]=1)([O-])=O.NC1C=CC(CC2N3C=CN=C3C(CC(OC)=O)=CN=2)=CC=1.[Cl:47][C:48]1[CH:49]=[C:50]([CH:54]=[CH:55][C:56]=1[Cl:57])[C:51](O)=[O:52].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>CO.C(OCC)(=O)C.[Pd].ClCCl>[Cl:47][C:48]1[CH:49]=[C:50]([CH:54]=[CH:55][C:56]=1[Cl:57])[C:51]([NH:1][C:4]1[CH:24]=[CH:23][C:7]([CH2:8][C:9]2[N:14]3[CH:15]=[CH:16][N:17]=[C:13]3[C:12]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:11][N:10]=2)=[CH:6][CH:5]=1)=[O:52]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 6

HCID 58173,4-Dichlorobenzoic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57542079Methyl [5-(4-aminobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetateHCID 57542081Methyl [5-(4-nitrobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate

Product 1

HCID 57542077Methyl (5-{4-[(3,4-dichloro-benzoyl)amino]benzyl}imidazo[1,2-c]pyrimidin-8-yl)acetateYield 70%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl [5-(4-nitrobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (28 mg, 0.09 mmol) and Pd/C (wet, 3 mg) in methanol (1 mL) was stirred under hydrogen atmosphere for 1 hour. After the removal of Pd/C by filtration through a Celite pad, the filtrate was concentrated in vacuo. The resulting crude methyl [5-(4-aminobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (26 mg, 0.09 mmol) was dissolved with dichloromethane (1 mL). To this solution was added 3,4-dichloro-benzoic acid (20.1 mg, 0.11 mmol), 1-hydroxybenzotriazole (14.2 mg, 0.11 mmol), triethylamine (0.037 mL, 0.26 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21.9 mg, 0.11 mmol) at room temperature. The mixture was stirred at room temperature overnight, and diluted with ethyl acetate. The solution was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative TLC (silica gel, chloroform:methanol, 19:1) to give methyl (5-{4-[(3,4-dichloro-benzoyl)amino]benzyl}imidazo[1,2-c]pyrimidin-8-yl)acetate (29 mg, 70%) as slightly yellow oil.

Workup

  1. customAfter the removal of Pd/C
  2. filtrationby filtration through a Celite pad
  3. concentrationthe filtrate was concentrated in vacuo
  4. stirringThe mixture was stirred at room temperature overnight
  5. washThe solution was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by preparative TLC (silica gel, chloroform:methanol, 19:1)

Sources & evidence

ORD record
ord-fe13bb9cf76b457181ff68c32f5c2051
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07750014B2

Reaction notes

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