Quinaldic Acid → HCID 22353329, compound

HRID 895491Notes

Reaction equation

HRID 895491 reaction equation
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl:47][C:48]1[CH:53]=[CH:52][C:51]([C:54]2[N:59]=[C:58]([NH:60][CH2:61][CH2:62][NH:63][C:64](=[O:66])[CH3:65])[CH:57]=[C:56]([N:67]3[CH2:72][CH2:71][NH:70][CH2:69][CH2:68]3)[N:55]=2)=[CH:50][CH:49]=1>CN1C(=O)CCC1>[Cl:47][C:48]1[CH:49]=[CH:50][C:51]([C:54]2[N:59]=[C:58]([NH:60][CH2:61][CH2:62][NH:63][C:64](=[O:66])[CH3:65])[CH:57]=[C:56]([N:67]3[CH2:72][CH2:71][N:70]([C:1]([C:2]4[CH:11]=[CH:10][C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[N:3]=4)=[O:13])[CH2:69][CH2:68]3)[N:55]=2)=[CH:52][CH:53]=1

Participants

6

Reactant 4

HCID 7124Quinaldic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22353300HCID 22353300, compound

Product 1

HCID 22353329HCID 22353329, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent4×

Procedure

A solution of quinaldic acid (60 μl of a 0.3M solution in NMP), HATU (60 μl of a 0.3M solution in NMP) and diisopropylethylamine (60 μl of a 0.3M solution in NMP) was shaken at ambient temperature in a well of a 96 position microtitre plate for 5 min. N-(2-{[2-(4-chlorophenyl)-6-piperazin-1-ylpyrimidin-4-yl]amino}ethyl)acetamide (30 μl of a 0.3M solution in NMP) was then added and the mixture shaken for a further 12 hr. Purification via ion exchange silica (SCX) yields the title compound.

Workup

  1. customPurification via ion exchange silica (SCX)

Sources & evidence

ORD record
ord-b4a1adcdbc084637bc49486d600d40fd
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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