Triethylamine → HCID 178490590, compound

HRID 452978Notes

Reaction equation

HRID 452978 reaction equation
[C:1]([C:5]1[O:9][C:8](=[NH:10])[N:7]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:46][O:47][C:48]1[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][C:49]=1[C:50](O)=[O:51]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[O:9]/[C:8](=[N:10]\[C:50](=[O:51])[C:49]2[CH:53]=[C:54]([C:57]([F:59])([F:60])[F:58])[CH:55]=[CH:56][C:48]=2[O:47][CH3:46])/[N:7]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 135859092-Methoxy-5-(trifluoromethyl)benzoic acidHCID 66643286(r)-5-Tert-butyl-3-((tetrahydrofuran-2-yl)methyl)oxazol-2(3h)-imine

Product 1

HCID 178490590HCID 178490590, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 66A (100 mg, 0.45 mmol) in tetrahydrofuran (4 mL) was added N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (85.0 mg, 0.45 mmol), 1-hydroxybenzotriazole (68.3 mg, 0.45 mmol), triethylamine (93 μL, 0.67 mmol) and 2-methoxy-5-trifluoromethylbenzoic acid (Alfa) (98.0 mg, 0.45 mmol). The mixture was stirred at 60° C. overnight, cooled to room temperature, diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% ethyl acetate in hexanes) to provide the title product. MS (ESI+) m/z 428 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 1.15-1.19 (m, 1H), 1.20 (s, 9H), 1.61-1.72 (m, 1H), 1.83-1.96 (m, 2H), 2.02-2.15 (m, 1H), 3.68 (dd, J=14.3, 7.1 Hz, 1H), 3.75-3.87 (m, 2H), 3.89 (s, 3 H), 4.02-4.12 (m, 1H), 4.14-4.25 (m, 1H), 6.53 (s, 1H), 6.97 (d, J=8.7 Hz, 1H), 7.58 (dd, J=8.7, 2.4 Hz, 1H), 8.06 (d, J=2.0 Hz, 1H).

Workup

  1. temperaturecooled to room temperature
  2. washwashed with 1 M aqueous NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d1d3f8f82a3f46c2a46e6099a22a6936
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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