Triethylamine → 8-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-7-carboxamide

HRID 925609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925609
[NH2:1][C:2]1[C:3]([C:13]([OH:15])=O)=[CH:4][C:5]([Br:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:43][C@H:44]1[CH2:49][CH2:48][CH2:47][CH2:46][C@@H:45]1[OH:50].C(N(CC)CC)C>ClCCl>[NH2:1][C:2]1[C:3]([C:13]([NH:43][C@H:44]2[CH2:49][CH2:48][CH2:47][CH2:46][C@@H:45]2[OH:50])=[O:15])=[CH:4][C:5]([Br:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7057408(1S,2S)-2-aminocyclohexanolHCID 336958818-Amino-5-bromoquinoline-7-carboxylic acid

Produkt 1

HCID 892161208-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-7-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 8-amino-5-bromoquinoline-7-carboxylic acid (1.00 g, 3.74 mmol) in 20 mL of dichloromethane was added (1H-1,2,3-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (1.99 g, 4.49 mmol), (1S,2S)-2-aminocyclohexanol (0.517 g, 4.49 mmol), and triethylamine (1.04 mL, 7.49 mmol). After 3 h, a brown solid was collected and washed with dichloromethane and water to provide 8-amino-5-bromo-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-7-carboxamide that gave a mass ion (ES+) of 365.9 (81Br) for [M+H]+.

Aufarbeitung

  1. customa brown solid was collected
  2. washwashed with dichloromethane and water

Quellen und Nachweise

ORD-Eintrag
ord-187e53b5ad404cfc8d4d96b48f62daaa
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284312B2

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