Quinaldic Acid → HCID 22353489, compound

HRID 895499Notes

Reaction equation

HRID 895499 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.[NH2:47][CH2:48][CH2:49][NH:50][C:51]1[N:56]=[C:55]([C:57]2[CH:62]=[CH:61][C:60]([Cl:63])=[CH:59][CH:58]=2)[N:54]=[C:53]([NH:64][CH2:65][CH2:66][NH:67][C:68](=[O:70])[CH3:69])[CH:52]=1>CN1C(=O)CCC1>[C:68]([NH:67][CH2:66][CH2:65][NH:64][C:53]1[N:54]=[C:55]([C:57]2[CH:62]=[CH:61][C:60]([Cl:63])=[CH:59][CH:58]=2)[N:56]=[C:51]([NH:50][CH2:49][CH2:48][NH:47][C:1]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[O:13])[CH:52]=1)(=[O:70])[CH3:69]

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 22378879HCID 22378879, compound

Product 1

HCID 22353489HCID 22353489, 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-{[6-[(2-aminoethyl)amino]-2-(4-chlorophenyl)pyrimidin-4-yl]amino}ethyl) acetamide (30 μl of a 0.3M solution in NMP) was then added and the mixture shaken for a further 48 hrs. Purification via ion exchange silica (SCX) yields the title compound. LCMS (Method A) RT=2.58 min; m/z (ES+) 504 (MH)+

Workup

  1. customPurification via ion exchange silica (SCX)

Sources & evidence

ORD record
ord-eec2602480294bc9ad73023fc09522a2
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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