Piperidine → HCID 22353323, compound

HRID 895484Notes

Reaction equation

HRID 895484 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]([NH:20][C:21](=[O:25])[C:22]([OH:24])=O)[CH:9]=1)(=[O:3])[CH3:2].CN(C(ON1N=N[C:36]2[CH:37]=[CH:38][CH:39]=[N:40][C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.N1CCCCC1>CN1C(=O)CCC1>[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:11]=[C:10]([NH:20][C:21](=[O:25])[C:22](=[O:24])[N:40]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)[CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22353453HCID 22353453, compound

Product 1

HCID 22353323HCID 22353323, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of [(6-{[2-(acetylamino)ethyl]amino}-2-phenylpyrimidin-4-yl)amino](oxo)acetic acid (50 mg) in NMP (2.5 ml) were added HATU (51 mg) and N,N-diisopropylethylamine (25 μl). The mixture was stirred at room temperature for 15 min then piperidine (90 μl) added and the solution left for 16 hrs. After this time, the solvent was removed in vacuo. Purification via flash chromatography on silica gel using ethyl acetate as the eluent furnished the correct material (10 mg).

Workup

  1. waitthe solution left for 16 hrs
  2. customAfter this time, the solvent was removed in vacuo
  3. customPurification via flash chromatography on silica gel

Sources & evidence

ORD record
ord-2e483be9d67d40f6908fb04b87ba4f98
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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