Dimethylformamide → HCID 69845455, compound

HRID 2260121Notes

Reaction equation

HRID 2260121 reaction equation
S(O[CH2:12][CH2:13][N:14]1[C:18]2=[CH:19][C:20]3[N:21]=[C:22]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([F:35])[CH:28]=4)[CH:23]=[N:24][C:25]=3[CH:26]=[C:17]2[CH:16]=[N:15]1)(C1C=CC(C)=CC=1)(=O)=O.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.CN(C=O)C>O>[N:36]1([CH2:12][CH2:13][N:14]2[C:18]3=[CH:19][C:20]4[N:21]=[C:22]([C:27]5[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([F:35])[CH:28]=5)[CH:23]=[N:24][C:25]=4[CH:26]=[C:17]3[CH:16]=[N:15]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 18999848HCID 18999848, compound

Product 1

HCID 69845455HCID 69845455, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-tosyloxyethyl)-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (0.3 g), piperdine (0.11 g) and 20 ml of anhydrous DMF is stirred at room temperature overnight. The mixture is heated to gentle reflux for 21/2 hours. After cooling, it is poured into water and the precipitate is filtered, washed with water and air dried. This is then purified by chromatography using (3:7-1:9) methylene chloride in ethylacetate as eluent. 0.220 g of desired product to obtain 1-(2-piperdin-1-ylethyl)-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (m.p. 117°-120° C. (dec)).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto gentle reflux for 21/2 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate is filtered
  5. washwashed with water and air
  6. customdried
  7. customThis is then purified by chromatography

Sources & evidence

ORD record
ord-2a7467a3e2f841c1b019ab7b656f71bf
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

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