Dimethylformamide → Ammonium Hydroxide

HRID 593518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593518
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[C:6]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[C:5]2[CH3:26].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+].CN(C=[O:37])C>>[NH4+:7].[OH-:37].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]3[N:27]=[N:28][NH:29][N:17]=3)=[CH:18][CH:19]=1)[C:6]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[C:5]2[CH3:26]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 582156974-(5-chloro-3-methyl-2-pyridin-3-yl-1H-indol-1-ylmethyl)-benzonitrile

Produkt 2

HCID 14923Ammonium HydroxideAusbeute 0,1 %HCID 582157675-chloro-3-methyl-2-pyridin-3-yl-1-[4-(2H-tetrazol-5-yl)-benzyl]-1H-indole

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 4-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzonitrile (Example 17, 179 mg, 0.5 mmol) in DMF (5 mL) is added sodium azide (97 mg, 1.5 mmol) and ammonium chloride (80 mg, 1.5 mmol) and the mixture is heated to 120° C. The reaction mixture is cooled to room temperature and filtered. The filtrate is purified by reverse phase HPLC with Xbridge C18 and a gradient of 0.1% NH4OH in acetonitrile to give 5-chloro-3-methyl-2-pyridin-3-yl-1-[4-(2H-tetrazol-5-yl)-benzyl]-1H-indole. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.21 (s, 3H), 5.34 (s, 2H), 6.81 (d, J=8.1 Hz, 2H), 7.11 (br. s., 1H), 7.17 (dd, J=8.7, 2.1 Hz, 1H), 7.48-7.53 (m, 2H), 7.67 (d, J=2.0 Hz, 1H), 7.77 (d, J=8.3 Hz, 2H), 7.80-7.84 (m, 1H), 8.60 (d, J=1.5 Hz, 1H), 8.62 (dd, J=4.8, 1.5 Hz, 1H). HRMS (ESI) m/z 401.1276 [(M+H)+ Calcd for C22H18N6Cl: 401.1281].

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate is purified by reverse phase HPLC with Xbridge C18

Quellen und Nachweise

ORD-Eintrag
ord-2d043615e1dd4d2497a7cdb8165ca596
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242963B2

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