Water → HCID 18617628, compound

HRID 1264220Notes

Reaction equation

HRID 1264220 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:31])[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:23]=[CH:24][C:25](OC)=[N:26][CH:27]=4)=[CH:18][C:17]=3[CH3:30])[CH:10]=2)[NH:5][CH:4]=1)#[N:2].Cl.[NH+]1C=CC=CC=1.[OH2:39]>>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:31])[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:27](=[O:39])[NH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][C:17]=3[CH3:30])[CH:10]=2)[NH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 962WaterHCID 18617735HCID 18617735, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 18617628HCID 18617628, compound

Conditions

Temperature
160 °C

Procedure

A mixture of N-[2-(3-Cyano-1H-indol-5-yl)-ethyl]-4-(2-methoxy-pyridin-5-yl)-2-methyl-benzamide (146 mg, 0.35 mmol) (reference example 1n) and pyridinium hydrochloride (3 g) is heated to 160° C. and stirred at this temperature for 3 minutes. The liquid is then cooled and mixed with water. The resulting precipitated solid is filtered, washed with water (3×) then dried under vacuum to give 133 mg of th title compound as a solid. This material is used without further purification. MS (ion spray) m/z 397 (M+H).

Workup

  1. temperatureThe liquid is then cooled
  2. customThe resulting precipitated solid
  3. filtrationis filtered
  4. washwashed with water (3×)
  5. customthen dried under vacuum

Sources & evidence

ORD record
ord-97899941137b4a1fb9a9d6fa2fb8d517
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

Loading…