Trifluoroacetic acid → HCID 58972444, compound

HRID 2264513Notes

Reaction equation

HRID 2264513 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#N)=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:25]([O:29]C(N1CCC(NC2N=CC(O)=CN=2)CC1)=O)(C)(C)C.BrCCCOC1CCCCO1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O.N1CCC(NC2N=CC(OCC#N)=CN=2)CC1>CN(C=O)C.ClCCl>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[N:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][CH2:25][OH:29])=[CH:19][N:20]=2)[CH2:12][CH2:13]1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 58972425HCID 58972425, compoundHCID 68779108HCID 68779108, compoundHCID 68779156HCID 68779156, compound

Product 1

HCID 58972444HCID 58972444, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The compound was prepared in analogy to the synthesis of 4-(5-cyanomethoxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (intermediate C32/step 1) from 4-(5-hydroxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (intermediate C31/step 2) by reaction with rac-2-(3-bromopropoxy)tetrahydro-2H-pyran (commercially available) and potassium carbonate in DMF at 100° C., followed by BOC and THP cleavage with 90% trifluoroacetic acid in dichloromethane at rt for 16 h in analogy to the procedure described for [2-(piperidin-4-ylamino)-pyrimidin-5-yloxy]-acetonitrile (intermediate C32/step 2). MS (ISP): 253.0 [M+H]+.

Sources & evidence

ORD record
ord-0bd63efd1c84433ea435761b796bf626
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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