Triethylamine → HCID 178433719, compound

HRID 487294Notes

Reaction equation

HRID 487294 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[CH2:11][N:12]1[C:16]2=[N:17][C:18]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:19][C:20](=[O:21])[C:15]2=[C:14]([CH3:28])[NH:13]1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][C:53]=2[S:55](Cl)(=[O:57])=[O:56])[CH:48]=[CH:47][CH:46]=1>N1C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:55]([C:53]2[CH:52]=[CH:51][CH:50]=[C:49]3[C:54]=2[N:45]=[CH:46][CH:47]=[CH:48]3)(=[O:56])=[O:57])=[CH:6][C:5]=1[CH2:11][N:12]1[C:16]2=[N:17][C:18]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:19][C:20](=[O:21])[C:15]2=[C:14]([CH3:28])[NH:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 292208-Quinolinesulfonyl chlorideHCID 178433717HCID 178433717, compound

Product 1

HCID 178433719HCID 178433719, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(2-chloro-5-aminophenylmethyl)-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one dihydrochloride salt (0.55 g, 1.4 mmol), pyridine (10 ml) and triethylamine (0.18 ml, 1.36 mmol) was stirred at 0° C. under argon for 20 minutes and dimethylaminopyridine (0.016 g, 0.14 mmol) and 8-quinoline sulfonyl chloride (0.37 g, 1.6 mmol) were added. The mixture was stirred at 0° C. for 2.5 hours and poured into ice-water with stirring. The product was collected by filtration to afford 0.66 g (88%) of 1-[2-chloro-5-((8-quinolinylsulfonyl)amino)phenylmethyl]-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one as a tan powder, m.p. 325° C. (dec.) when dried at 100° C. for 24 hours in high vacuum.

Workup

  1. stirringwith stirring
  2. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-4aa207af6e244eb9b8ef9b0e2c9752c0
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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