Hydrochloric Acid → HCID 58972445, compound

HRID 2264504Notes

Reaction equation

HRID 2264504 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19]([NH:21][CH2:22][CH2:23][OH:24])[N:18]=[C:17]([O:25][CH3:26])[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:27]([O:31]C(N1CCC(NC2N=C(Cl)N=C(OC)N=2)CC1)=O)([CH3:30])([CH3:29])[CH3:28].NCC(OC(C)(C)C)=O.C(N(C(C)C)C(C)C)C.Cl.COC1N=C(NC2CCNCC2)N=C(NCCO)N=1>C(#N)C.O1CCOCC1.CO>[C:27]([O:31][C:23](=[O:24])[CH2:22][NH:21][C:19]1[N:18]=[C:17]([O:25][CH3:26])[N:16]=[C:15]([NH:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[N:20]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 58972439HCID 58972439, compoundHCID 68781601HCID 68781601, compoundHCID 86615299HCID 86615299, compound

Product 1

HCID 58972445HCID 58972445, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

The compound was prepared in analogy to the synthesis of 4-[4-(2-hydroxy-ethylamino)-6-methoxy-[1,3,5]triazin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (intermediate C26/step 2) from 4-(4-chloro-6-methoxy-[1,3,5]triazin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (intermediate C26/step 1) and tert-butyl glycinate and N-ethyl diisopropylamine in acetonitrile at 50° C., followed by BOC cleavage with 4 M HCl in dioxane and methanol at rt 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): 339.2 [M+H]+.

Sources & evidence

ORD record
ord-93108560d1724a838b2a138973436f94
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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