Diisopropylethylamine → 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-2-naphthamide

HRID 724225Notes

Reaction equation

HRID 724225 reaction equation
[OH:1][C:2]1([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20](O)=[O:21])[CH:14]=[CH:13]3)[C:9]2[N:5]([CH:6]=[N:7][CH:8]=2)[CH2:4][CH2:3]1.Cl.C([N:26]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[OH:1][C:2]1([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20]([NH2:26])=[O:21])[CH:14]=[CH:13]3)[C:9]2[N:5]([CH:6]=[N:7][CH:8]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 218796156-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-7-yl)-2-naphthoic acid

Product 1

HCID 99658856-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-2-naphthamideYield 11.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-2-naphthoic acid (449 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (321 mg) and 1-hydroxy-1H-benzotriazole monohydrate (301 mg) were dissolved in DMF (7.6 ml), and diisopropylethylamine (216 mg) was added with stirring under ice-cooling. The reaction mixture was warmed to room temperature and stirred for 18 h. Silica gel (3 g) was added to the reaction mixture and the mixture was concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol containing aqueous ammonia (7%): 19/1) and the eluate was concentrated to dryness. The residue was recrystallized from ethanol to give the title compound (53 mg).

Workup

  1. temperaturecooling
  2. stirringstirred for 18 h
  3. additionSilica gel (3 g) was added to the reaction mixture
  4. concentrationthe mixture was concentrated to dryness under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol containing aqueous ammonia (7%): 19/1)
  6. concentrationthe eluate was concentrated to dryness
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-30de7ef3470c4e8ebb77b82b1b0250b7
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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