Butyric Acid → HCID 57510018, compound

HRID 624168Notes

Reaction equation

HRID 624168 reaction equation
[OH:1]/[N:2]=[C:3](/[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])=[CH:7][CH:6]=1)\[NH2:4].[C:23](O)(=O)[CH2:24][CH2:25][CH3:26].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([C:23]1[O:1][N:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]3[CH2:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:22]3)=[O:13])=[CH:7][CH:6]=2)[N:4]=1)[CH2:25][CH3:26]

Participants

8

Reactant 5

HCID 264Butyric AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 87561227HCID 87561227, compound

Product 1

HCID 57510018HCID 57510018, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 4 mL vial was mixed (Z)—N-(4-(N′-hydroxycarbamimidoyl)phenyl)isoindoline-2-carboxamide (50 mg, 0.169 mmol), butyric acid (0.017 ml, 0.186 mmol), 1-hydroxybenzotriazole hydrate (12.92 mg, 0.084 mmol), and N-methylmorpholine (0.056 ml, 0.506 mmol) in anhydrous dimethylformamide (2 ml). To this solution was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (48.5 mg, 0.253 mmol) and the mixture was stirred overnight at ambient temperature. The solution was diluted with ethyl acetate and washed with water, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried with sodium sulfate, decanted, and concentrated. The residue was taken up in anhydrous toluene (1 ml), and the mixture was heated at 110° C. for 2 days. The reaction was diluted with water; and the solids that formed were filtered and washed with water and ether to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.68 (s, 1H), 7.89-7.91 (m, 2H), 7.78-7.80 (m, 2H), 7.36-7.40 (m, 2H), 7.30-7.34 (m, 2H), 4.76-4.85 (m, 4H), 2.96 (t, J=7.4 Hz, 2H), 1.81 (hex, J=7.4 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H); MS (ESI(−)) m/e347 (M−H)−.

Workup

  1. washwashed with water, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customdecanted
  4. concentrationconcentrated
  5. temperaturethe mixture was heated at 110° C. for 2 days
  6. additionThe reaction was diluted with water
  7. customand the solids that formed
  8. filtrationwere filtered
  9. washwashed with water and ether

Sources & evidence

ORD record
ord-1f32221fa586425aa95a68556536a6c8
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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