4-Phenylbutyric Acid → N-{4-[(4-phenylbutanoyl)amino]phenyl}-1,3-dihydro-2H-isoindole-2-carboxamide

HRID 624120Notes

Reaction equation

HRID 624120 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[C:20]1([CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O.CO.C(Cl)Cl>[C:20]1([CH2:26][CH2:27][CH2:28][C:29]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9]([N:11]3[CH2:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:12]3)=[O:10])=[CH:6][CH:7]=2)=[O:30])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 5

HCID 47754-Phenylbutyric AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 62231518N-(4-aminophenyl)isoindoline-2-carboxamide

Product 1

HCID 57509917N-{4-[(4-phenylbutanoyl)amino]phenyl}-1,3-dihydro-2H-isoindole-2-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of N-(4-aminophenyl)isoindoline-2-carboxamide (100 mg, 0.395 mmol), 4-phenylbutanoic acid (78 mg, 0.474 mmol), 1-hydroxybenzotriazole hydrate (66.5 mg, 0.434 mmol) and N-methylmorpholine (0.109 ml, 0.987 mmol) in dimethylformamide (1.771 ml) at room temperature was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (136 mg, 0.711 mmol). The mixture was stirred overnight and diluted with water (10 ml); the resulting suspension was filtered with water washes to give product with an impurity. This solid was suspended in 2% methanol/methylene chloride and filtered to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.78-2.00 (m, 2H), 2.30 (t, J=7.3 Hz, 2H), 2.62 (t, J=7.5 Hz, 2H), 4.75 (s, 4H), 7.08-7.41 (m, 9H), 7.46 (s, 4H), 8.26 (s, 1H), 9.73 (s, 1H); (ESI(+)) m/e 400 (M+H)+.

Workup

  1. filtrationthe resulting suspension was filtered with water
  2. customto give product with an impurity
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f072037d75de4e19994f18bfdd3f7aaa
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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