Triethylamine → Ammonium Acetate

HRID 78481Notes

Reaction equation

HRID 78481 reaction equation
Br.[CH3:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH2:11][CH2:12][O:13][CH2:14][C:9]=2[S:8][C:7]1=[NH:15].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[Cl:45][C:46]1[CH:47]=[CH:48][C:49]([O:55][CH3:56])=[C:50]([CH:54]=1)[C:51]([OH:53])=[O:52]>O1CCCC1.C(OCC)(=O)C>[C:51]([O-:53])(=[O:52])[CH3:50].[NH4+:6].[Cl:45][C:46]1[CH:47]=[CH:48][C:49]([O:55][CH3:56])=[C:50]([CH:54]=1)[C:51](/[N:15]=[C:7]1\[S:8][C:9]2[CH2:14][O:13][CH2:12][CH2:11][C:10]=2[N:6]\1[CH2:5][CH2:4][O:3][CH3:2])=[O:52]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 769705-Chloro-o-anisic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 686233401-(2-methoxyethyl)-6,7-dihydro-1H-pyrano[4,3-d]thiazol-2(4H)-imine hydrobromide

Product 2

HCID 517165Ammonium AcetateHCID 178495756HCID 178495756, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 218B (150.0 mg, 0.51 mmol) in tetrahydrofuran (10 mL) was added N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (97.0 mg, 0.51 mmol), 1-hydroxybenzotriazole (69.0 mg, 0.51 mmol), triethylamine (178.0 μL, 1.28 mmol), and 5-chloro-2-methoxybenzoic acid (Aldrich) (95.0 mg, 0.51 mmol). The mixture was stirred overnight at 80° C., and then diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. Purification by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile: ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes afforded the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 2.75 (t, J=5.4 Hz, 2H), 3.25 (s, 3H), 3.69 (t, J=5.3 Hz, 2H), 3.80 (s, 3H), 3.95 (t, J=5.4 Hz, 1H), 4.27 (t, J=5.3 Hz, 2H), 4.58 (s, 2H), 7.12 (d, J=8.8 Hz, 1H), 7.46 (dd, J=9.0, 2.9 Hz, 1H), 7.69 (d, J=2.7 Hz, 1H); MS (ESI+) m/z 383 (M+H)+. Anal. Calculated for C17H19ClN2O4S: C, 53.33; H, 5.00; N, 7.32. Found: C, 53.21; H, 4.80; N, 7.27.

Workup

  1. washwashed with 1 M aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)

Sources & evidence

ORD record
ord-6bc51277608841639b6dae6fcf9478d4
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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