Hydrochloric Acid → HCID 58972459, compound

HRID 2264512Notes

Reaction equation

HRID 2264512 reaction equation
C(OC(N1CCC(NC2N=CC(OCC#N)=CN=2)CC1)=O)(C)(C)C.C(OC([N:32]1[CH2:37][CH2:36][CH:35]([NH:38][C:39]2[N:44]=[CH:43][C:42]([OH:45])=[CH:41][N:40]=2)[CH2:34][CH2:33]1)=O)(C)(C)C.CC1(C)[O:51][CH:50]([CH2:52]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:49][O:48]1.C(=O)([O-])[O-].[K+].[K+].Cl.COC1N=C(NC2CCNCC2)N=C(NCCO)N=1>CN(C=O)C.O1CCOCC1.C(O)C>[NH:32]1[CH2:33][CH2:34][CH:35]([NH:38][C:39]2[N:40]=[CH:41][C:42]([O:45][CH2:52][CH:50]([OH:51])[CH2:49][OH:48])=[CH:43][N:44]=2)[CH2:36][CH2:37]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateHCID 58972439HCID 58972439, compoundHCID 68779108HCID 68779108, compoundHCID 68779156HCID 68779156, compound

Product 1

HCID 58972459HCID 58972459, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

The title 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-toluene-4-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (commercially available) and potassium carbonate in DMF at rt for 48 h, followed by BOC and isopropylidene cleavage with 4 M HCl in dioxane and ethanol at 60° C. in analogy to the procedure described for 2-[4-methoxy-6-(piperidin-4-ylamino)-[1,3,5]triazin-2-ylamino]-ethanol (intermediate C26/step 3) and subsequent ion exchange chromatography on Q-Sepharose Fast Flow. MS (ISP): 269.1 [M+H]+.

Sources & evidence

ORD record
ord-0b17bad8f7e5471f81cb55f3ff280d2f
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

Loading…