Triethylamine → HCID 178448419, compound

HRID 1028181Notes

Reaction equation

HRID 1028181 reaction equation
[CH2:1]([N:5]1[C:9]2[CH2:10][O:11][CH2:12][C:8]=2[S:7][C:6]1=[NH:13])[CH2:2][CH2:3][CH3:4].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:24][CH3:25])=[C:19]([CH:23]=1)[C:20](O)=[O:21].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>O1CCCC1>[CH2:1]([N:5]1[C:9]2[CH2:10][O:11][CH2:12][C:8]=2[S:7]/[C:6]/1=[N:13]\[C:20](=[O:21])[C:19]1[CH:23]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=1[O:24][CH3:25])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 769705-Chloro-o-anisic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68772367HCID 68772367, compound

Product 1

HCID 178448419HCID 178448419, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 17A (220 mg, 0.56 mmol) in tetrahydrofuran (10 mL) were added 5-chloro-2-methoxybenzoic acid (114 mg, 0.61 mmol, Aldrich), 1-hydroxybenzotriazole (93 mg, 0.61 mmol, Aldrich), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (117 mg, 0.61 mmol) and triethylamine (0.23 mL, 1.7 mmol, Aldrich). The reaction mixture was stirred at 80° C. for 2 h, then cooled and quenched with saturated NaHCO3 (10 mL). The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-100% EtOAc in hexanes) to afford 60 mg (30%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.3 Hz, 3H), 1.33 (t, 2H), 1.74 (t, 2H), 3.80 (s, 3H), 4.10 (t, J=7.3 Hz, 2H), 4.87-5.08 (m, J=1.7 Hz, 4H), 7.13 (d, J=8.8 Hz, 1H), 7.47 (dd, J=8.8, 3.1 Hz, 1H), 7.75 (d, J=3.1 Hz, 1H); MS (ESI+) m/z 367 (M+H)+; Anal. Calculated C17H19ClN2O3S: C, 55.66; H, 5.22; N, 7.64. Found: C, 55.46; H, 5.03; N, 7.74.

Workup

  1. temperaturecooled
  2. customquenched with saturated NaHCO3 (10 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-395a6e5aec18499e9a43022bf3fca50f
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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