Ammonium Chloride → N4-(5-Chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)-N1-(2-dimethylaminoethyl)-5-methoxy-N1-methylbenzene-1,2,4-triamine

HRID 1842696

Reaktionsgleichung

Reaktionsgleichung von HRID 1842696
[NH4+].[Cl-].[Cl:3][C:4]1[C:5]([C:29]2[CH:30]=[N:31][N:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=23)=[N:6][C:7]([NH:10][C:11]2[CH:16]=[C:15]([N+:17]([O-])=O)[C:14]([N:20]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH3:21])=[CH:13][C:12]=2[O:27][CH3:28])=[N:8][CH:9]=1>O.C(O)C.[Fe]>[Cl:3][C:4]1[C:5]([C:29]2[CH:30]=[N:31][N:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=23)=[N:6][C:7]([NH:10][C:11]2[CH:16]=[C:15]([NH2:17])[C:14]([N:20]([CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])[CH3:21])=[CH:13][C:12]=2[O:27][CH3:28])=[N:8][CH:9]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 71270273N-(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)-N'-(2-dimethylaminoethyl)-2-methoxy-N'-methyl-5-nitrobenzene-1,4-diamine2×

Produkt 1

HCID 86677330N4-(5-Chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)-N1-(2-dimethylaminoethyl)-5-methoxy-N1-methylbenzene-1,2,4-triamineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A solution of NH4Cl (45 mg, 0.85 mmol) in water (10 mL) was added in one portion to a stirred mixture of N-(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)-N′-(2-dimethylaminoethyl)-2-methoxy-N′-methyl-5-nitrobenzene-1,4-diamine (Intermediate 34, 600 mg, 1.21 mmol) and iron (405 mg, 7.24 mmol) in ethanol (30 mL). The resulting mixture was stirred at 105° C. for 3 h. The mixture was then concentrated in vacuo and the resulting residue was mixed with DMF (10 mL) and purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 0.35M methanolic ammonia in CH2Cl2 and pure fractions were concentrated in vacuo to give the title compound (530 mg, 94%) as a brown gum; 1H NMR: 2.16 (6H, d), 2.38 (2H, t), 2.66 (3H, d), 2.92 (2H, t), 3.66 (3H, s), 4.60 (2H, s), 6.78 (1H, s), 6.92 (1H, s), 7.12 (1H, t), 7.27-7.4 (1H, m), 8.38 (1H, s), 8.43 (1H, d), 8.49 (1H, s), 8.83 (1H, d), 8.95 (1H, s); m/z: ES+ MH+ 467.

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo
  2. additionthe resulting residue was mixed with DMF (10 mL)
  3. custompurified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. concentrationwere concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-29057b6da99344c9a37b7ae3ce834155
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946235B2

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