Dimethylformamide → HCID 10008274, compound

HRID 1669855Notes

Reaction equation

HRID 1669855 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=3)[N:11]=[C:10]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)[CH:9]=2)=[CH:4][CH:3]=1.[OH:31]N1C2N=CC=CC=2N=N1.C([N:44]([CH2:48][CH3:49])C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.CN([CH:65]=[O:66])C>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:44][CH2:48][CH2:49][C:65]([OH:66])=[O:31])=[O:20])=[CH:16][CH:15]=3)[N:11]=[C:10]([C:23]3[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67333819HCID 67333819, compound

Product 1

HCID 10008274HCID 10008274, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the intermediate from step E (1.07 g, 2.13 mmol) in DMF (20 mL) was added 1-hydroxy-7-azabenzo-triazole (435 mg, 3.19 mmol), N,N-diisopropylethyl amine (557 μL, 3.19 mmol) β-alanine-t-butyl ester hydrochloride (465 mg, 2.55 mmol) and 1-(3-(Dimethylamino)propyl-3-ethyl carbodiimide hydrochloride (489 mg, 2.55 mmol). The reaction was left stirring at room temperature for 18 hours. The reaction was diluted with EtOAc (150 mL), washed with 1N HCl, saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The yellow foam obtained was purified by flash chromatography using 2:5 ethylacetate-hexanes to give the title compound as a white solid. 1H NMR (CDCl3, 500 MHz): δ 7.75 (d, J=1.6 Hz, 2H), 7.73 (d, J=8.2 Hz, 2H), 7.56 (d, J=8.4 Hz, 2H), 7.31 (t, J=1.6 Hz, 1H), 7.18 (d, J=8.3 Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 6.92 (t, J=5.7 Hz, 1H), 6.65 (s, 1H), 5.39 (s, 2H), 3.7 (q, J=5.9 Hz, 2H), 2.57 (t, J=6.1 Hz, 2H), 1.47 (s, 9H). LC-MS: 2.95 min; (M-56)=572.1.

Workup

  1. waitThe reaction was left
  2. washwashed with 1N HCl, saturated NaHCO3 solution, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe yellow foam obtained
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-e21ad15a3a47417ab6d39afe238c6dc2
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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