Hydrochloric Acid → HCID 58972451, compound

HRID 2264514Notes

Reaction equation

HRID 2264514 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:24])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C([O:29]C(N1CCC(NC2N=CC(O)=CN=2)CC1)=O)(C)(C)C.BrCC(N)=O.C(=O)([O-])[O-].[K+].[K+].Cl.COC1N=C(NC2CCNCC2)N=C(NCCO)N=1>CN(C=O)C.O1CCOCC1>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[N:16]=[CH:17][C:18]([O:21][CH2:22][C:23]([NH2:24])=[O:29])=[CH:19][N:20]=2)[CH2:12][CH2:13]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 58972439HCID 58972439, compoundHCID 68779108HCID 68779108, compoundHCID 68779156HCID 68779156, compound

Product 1

HCID 58972451HCID 58972451, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 312751,4-DioxaneSolvent

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 2-bromo-acetamide and potassium carbonate in DMF at rt, followed by BOC cleavage with 4 M HCl in dioxane and DMF at 85° 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). MS (ISP): 252.0 [M+H]+.

Sources & evidence

ORD record
ord-c4a136f0dd0a4b868fcd13aae493c5e4
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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