Diisopropylethylamine → HCID 58171900, compound

HRID 2065578Notes

Reaction equation

HRID 2065578 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:50][O:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:59]=[N:60][C:61]([NH:64][C:65]3[CH:66]=[C:67]([NH2:72])[C:68]([CH3:71])=[N:69][CH:70]=3)=[N:62][CH:63]=2)=[CH:54][CH:53]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](=[O:16])[NH:72][C:67]1[C:68]([CH3:71])=[N:69][CH:70]=[C:65]([NH:64][C:61]2[N:60]=[CH:59][C:58]([C:55]3[CH:54]=[CH:53][C:52]([O:51][CH3:50])=[CH:57][CH:56]=3)=[CH:63][N:62]=2)[CH:66]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58171954N5-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2-methyl-pyridine-3,5-diamine

Product 1

HCID 58171900HCID 58171900, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (0.04 mmol) in DMF (1 mL) is added HATU (0.05 mmol) and DIEA (20.12 mmol). The resulting mixture is stirred for 2 min at rt and then N5-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2-methyl-pyridine-3,5-diamine 12 (0.032 mmol) is added. The reaction mixture is stirred at 45° C. for 12 h. The mixture is cooled down and directly purified by preparative LCMS to afford 2-{5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-2-methyl-pyridin-3-ylcarbamoyl}-piperidine-1-carboxylic acid tert-butyl ester 20. MS (m/z) (M+1)+: 519.1.

Workup

  1. stirringThe reaction mixture is stirred at 45° C. for 12 h
  2. temperatureThe mixture is cooled down
  3. customdirectly purified by preparative LCMS

Sources & evidence

ORD record
ord-19085a2006654b9f899ea3c47fb41f16
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

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