Triethylamine → 1-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetyl}piperidine-3-carboxamide

HRID 505542

Reaktionsgleichung

Reaktionsgleichung von HRID 505542
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH2:9][C:10](O)=[O:11])[N:7]=[N:8][C:4]=2[C:3]=1[O:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([Cl:24])[CH:17]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([C:31]([NH2:33])=[O:32])[CH2:26]1.[Cl-].C(N=C=NCCC[NH+](C)C)C.N1C2C(=NC=CC=2)N(O)N=1.C(N(CC)CC)C>CN(C=O)C.CO>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH2:9][C:10]([N:25]3[CH2:30][CH2:29][CH2:28][CH:27]([C:31]([NH2:33])=[O:32])[CH2:26]3)=[O:11])[N:7]=[N:8][C:4]=2[C:3]=1[O:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([Cl:24])[CH:17]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 929803-PiperidinecarboxamideHCID 181649HOAtHCID 53519323-(Ethyliminomethylideneamino)propyl-dimethylazanium chlorideHCID 68428094[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetic acid

Produkt 1

HCID 251097551-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetyl}piperidine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetic acid (13 mg, 0.036 mmol) (see step 2 in Example 16), piperidine-3-carboxamide (4.6 mg, 0.036 mmol), 3-{[(ethylimino)methylene]amino}-N,N-dimethylpropan-1-aminium chloride (6.9 mg, 0.036 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (4.9 mg, 0.036 mmol), and triethylamine (0.005 mL, 0.036 mmol) were dissolved in DMF (0.5 mL). After 1 hour, the reaction mixture was diluted with aqueous MeOH (1 mL) and purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. Product fractions were lyophilized to yield the title product. 1H NMR (DMSO-d6) δ 7.84 (m, 1H), 7.77 (d, J=4.4 Hz, 1H), 7.76 (s, 2H), 7.58 (m, 1H), 7.51 (m, 1H), 7.44 (m, 1H), 7.36 (m, 1H), 7.02 (m, 1H), 6.84 (m, 1H), 5.97 (m, 2H), 5.93 (m, 1H), 5.87 (m, 0.5H), 5.83 (m, 0.25H), 4.29 (m, 2H), 3.80 (m, 4H), 3.40 (m, 1H), 3.10 (m, 1H), 2.95 (m, 1H), 2.65 (m, 1H), 2.20 (m, 1H), 1.90 (m, 2H), 1.70 (m, 4H), 1.40 (m, 1H). HRMS (M+1)=473.0867.

Aufarbeitung

  1. custompurified by reverse phase chromatography
  2. washeluting with 30-95% MeCN/H2O+0.1% TFA

Quellen und Nachweise

ORD-Eintrag
ord-fead498b000642c8a1ca0b5054e0335a
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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