Triethylamine → HCID 178511967, Verbindung

HRID 423961

Reaktionsgleichung

Reaktionsgleichung von HRID 423961
[C:1]([C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1F)[C:6]([NH:8][C@H:9]([C:17]1[NH:18][CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[N:21]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])#[N:2].C(C1C=C(C=CC=1F)C(O)=O)#N.C([N:48](CC)CC)C.F[P-](F)(F)(F)(F)F.[N:60]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=[N:61]1>C1COCC1.O>[NH2:2][C:1]1[C:3]2[C:32](=[CH:31][CH:30]=[C:5]([C:6]([NH:8][C@H:9]([C:17]3[NH:18][CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([C:28](=[NH:48])[NH2:29])=[CH:24][CH:23]=4)[N:21]=3)[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:7])[CH:4]=2)[NH:61][N:60]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27739323-Cyano-4-fluorobenzoic acidHCID 178509599HCID 178509599, Verbindung

Produkt 1

HCID 178511967HCID 178511967, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Part B: 3-Cyano-N-{(S)-1-[4-(4-cyano-phenyl)-1H-imidazol-2-yl]-2-phenyl-ethyl}-4-fluoro-benzamide: A mixture of the compound of Example 176 Part A (100 mg, 0.28 mmol), 3-cyano-4-fluorobenzoic acid (46 mg, 0.28 mmol), triethylamine (0.085 mL, 0.61 mmol) and BOP (0.18 g, 0.4 mmol) in THF (5 mL) was stirred at rt overnight under N2. Reaction mixture was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with sat'd. NaHCO3 and brine and then dried over anhydrous Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/EtOAc) provided the amide product (88 mg, 72%). 1H NMR (500 MHz, CDCl3) δ 3.41 (dd, J=13.75, 7.15 Hz, 1H) 3.58 (dd, J=13.47, 7.97 Hz, 1H) 5.33 (q, J=7.70 Hz, 1H) 7.01-7.09 (m, 1H) 7.18-7.37 (m, 7H) 7.66 (d, J=8.25 Hz, 2H) 7.85 (d, J=8.25 Hz, 2H) 7.89-7.96 (m, 1H) 7.95-8.03 (m, 1H) 9.74 (s, 1H). m/z 436.1 (M+H)+.

Aufarbeitung

  1. customReaction mixture
  2. extractionextracted 3× with EtOAc
  3. washThe combined extracts were washed with sat'd
  4. dry with materialNaHCO3 and brine and then dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9ae21b6241614fcda10b79be34a8ffab
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101778B2

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