Urea → HCID 57424552, compound

HRID 1093261Notes

Reaction equation

HRID 1093261 reaction equation
NC(N)=O.[CH:5]12[O:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][N:7]([C:13]1[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](NCC)=[O:27])=[CH:21][CH:20]=3)[N:16]=[C:15]3[N:31]([CH:34]4CCN(C(OCC)=O)C[CH2:35]4)[N:32]=[CH:33][C:14]=13)[CH2:6]2.[NH2:45][C:46]1[CH:47]=[CH:48][C:49]([O:52][CH2:53][CH2:54][OH:55])=[N:50][CH:51]=1.[N+](C1C=CC(OCCO)=NC=1)([O-])=O.[H][H].NC1C=CC=CC=1>C(OCC)(=O)C.CO.[Pd]>[CH:5]12[O:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][N:7]([C:13]1[N:18]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([NH:25][C:26]([NH:45][C:46]4[CH:51]=[N:50][C:49]([O:52][CH2:53][CH2:54][OH:55])=[CH:48][CH:47]=4)=[O:27])=[CH:23][CH:24]=3)[N:16]=[C:15]3[N:31]([CH2:34][CH3:35])[N:32]=[CH:33][C:14]=13)[CH2:6]2

Participants

10

Reactant 6

HCID 1176UreaHCID 6115AnilineHCID 5879372-[(5-Nitropyridin-2-yl)oxy]ethan-1-olHCID 22061157HCID 22061157, compoundHCID 25262323ethyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-ethylureido)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57424552HCID 57424552, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A urea formation procedure similar to that used for the synthesis of ethyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-ethylureido)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate is used, utilizing 2-(5-aminopyridin-2-yloxy)ethanol (prepared by the reduction of 2-(5-nitropyridin-2-yloxy)ethanol in ethyl acetate and methanol with palladium on carbon and hydrogen gas) as the aniline component. (5%, MS=531.2 (M+H))

Sources & evidence

ORD record
ord-f4bc4410f34a4d05956948733dc4b471
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

Loading…