Diisopropylethylamine → HCID 58646742, compound

HRID 901994Notes

Reaction equation

HRID 901994 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@H:9]1[C@H:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1.[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([C:34](O)=[O:35])=[CH:28]2.Cl.C(N=C=N)C.ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1.C(OCC)(=O)C>[CH2:22]([O:21][C:19]([C@H:18]1[C@H:9]([NH:8][C:34]([C:29]2[NH:30][C:31]3[C:27]([CH:28]=2)=[CH:26][C:25]([Cl:24])=[CH:33][CH:32]=3)=[O:35])[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17]1)=[O:20])[CH3:23]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 181649HOAtHCID 21883477Ethylcarbodiimide hydrochlorideHCID 86605148HCID 86605148, compound

Product 1

HCID 58646742HCID 58646742, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of trans 2-amino-3-carboethoxy-1,2,3,4-tetrahydronaphthalene trifluoroacetic acid salt (130 mg, 0.39 mmol) and 5-chloroindole-2-carboxylic acid (92 mg, 0.47 mmol) in tetrahydrofuran (8 mL) at room temperature under nitrogen was added 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (153 mg, 0.78 mmol), 1-hydroxy-7-azabenzotriazole (106, 0.78 mmol), and diisopropylethylamine (0.14 mL, 0.78 mmol). After 2 h, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with 1.0 M aqueous hydrochloric acid solution, 1.0 M aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and concentrated under vacuum. The resulting residue was suspended in methanol. The suspension was filtered and the solid was washed with methanol to obtain the title compound (120 mg, 77%). 13C NMR (400 MHz, d8-tetrahydrofuran) δ 173.5, 161.3, 136.1, 135.2, 135.0, 134.6, 129.8, 129.5, 129.1, 126.9, 126.8, 126.0, 124.4, 121.5, 114.0, 101.8, 61.1, 48.5, 46.5, 36.0, 32.5, 14.5. 1H NMR (400 MHz, d8-tetrahydrofuran) δ 11.18 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.56 (s, 1H), 7.38 (d, J=7.8 Hz, 1H), 7.04-7.17 (m, 4H), 6.89 (s, 1H), 4.62 (m, 1H), 4.05 (q, J=7.0 Hz, 2H), 3.15-3.26 (m, 2H), 2.87-3.09 (m, 3H), 1.11 (t, J=7.0 Hz, 3H). MS [M+H]+, 397; [M−H]−, 395.

Workup

  1. washThe organic layer was washed with 1.0 M aqueous hydrochloric acid solution, 1.0 M aqueous sodium hydroxide solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. filtrationThe suspension was filtered
  5. washthe solid was washed with methanol

Sources & evidence

ORD record
ord-b5cb2f790c9f4f7d84023326ad64ccb0
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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