Diisopropylethylamine → Tert-butyl-(2S)-3,3-dimethyl-2-({4-[3-(1-quinolin-6-ylcyclopropyl)-[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoyl}amino)butanoate

HRID 2245982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245982
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]4[N:18]5[N:19]=[C:20]([C:23]6[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=6)[CH:21]=[N:22][C:17]5=[N:16][N:15]=4)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:33][C@@H:34]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:43][C:42]([CH3:45])([CH3:44])[C@H:34]([NH:33][C:27](=[O:28])[C:26]1[CH:25]=[CH:24][C:23]([C:20]2[CH:21]=[N:22][C:17]3[N:18]([C:14]([C:11]4([C:7]5[CH:6]=[C:5]6[C:10](=[CH:9][CH:8]=5)[N:1]=[CH:2][CH:3]=[CH:4]6)[CH2:13][CH2:12]4)=[N:15][N:16]=3)[N:19]=2)=[CH:31][CH:30]=1)[C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 56776989tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochlorideHCID 592163304-[3-(1-Quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoic acid

Produkt 1

HCID 59216337Tert-butyl-(2S)-3,3-dimethyl-2-({4-[3-(1-quinolin-6-ylcyclopropyl)-[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoyl}amino)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 4-[3-(1-quinolin-6-ylcyclopropyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoic acid (40 mg, 0.10 mmol), tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochloride (26 mg, 0.12 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (45.5 mg, 0.103 mmol), and N,N-diisopropylethylamine (60 μL, 0.34 mmol) in methylene chloride (1.5 mL) was stirred at RT overnight. The mixture was diluted with DCM, and washed with saturated NaHCO3 solution, water and brine, dried over Na2SO4, filtered, and concentrated to yield desired product which was directly used in the next step without further purification.

Aufarbeitung

  1. washwashed with saturated NaHCO3 solution, water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-318a839bc25942de98c0beb456f5b600
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683060B2

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