Triethylamine → HCID 178436585, Verbindung

HRID 1020920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020920
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C@@H:15]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][C:26]=3[CH2:33][CH3:34])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:13][CH:14]=2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.N[C@H](C1NC=C(C2C=CC(C(N)=O)=CC=2)N=1)CC1C=CC=CC=1>C1COCC1>[NH2:32][CH2:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([NH:23][C@H:15]([C:12]2[NH:13][CH:14]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([C:1](=[O:3])[NH2:2])=[CH:9][CH:8]=3)[N:11]=2)[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:35])=[C:26]([CH2:33][CH3:34])[CH:27]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178436584HCID 178436584, VerbindungHCID 178513610HCID 178513610, Verbindung

Produkt 1

HCID 178436585HCID 178436585, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Part E: N—{(S)-1-[4-(4-Carbamoyl-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-4-cyano-2-ethyl-benzamide: The product from Example 143 Part D (90 mg, 0.51 mmol), Bop reagent (265 mg, 0.61 mmol), and triethylamine (0.42 mL, 1.5 mmol) were added together with 5 mL of THF. The mixture was stirred at RT under N2 for 15 minutes and (S)-4-(2-(1-amino-2-phenylethyl)-1H-imidazol-4-yl)benzamide prepared using the methods described in Examples 2 and 28 (365 mg, 0.51 mg) was added. The resulting mixture was heated at 75° C. for 70 minutes. The THF was removed, and the residue was dissolved in EtOAc. It was washed with waster and brine, dried over MgSO4, concentrated, and purified by flash chromatography (silica, EtOAc/hexane) to give 80 mg of the desired product. MS: 464.4 (M+1)+.

Aufarbeitung

  1. additionwas added
  2. temperatureThe resulting mixture was heated at 75° C. for 70 minutes
  3. customThe THF was removed
  4. dissolutionthe residue was dissolved in EtOAc
  5. washIt was washed with waster and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (silica, EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-aba7f80f04404cc794d404563dc51b9e
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716492B2

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