Urea → HCID 45488078, compound

HRID 1093260Notes

Reaction equation

HRID 1093260 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.[N:45]1([C:50]2[CH:56]=[CH:55][C:53]([NH2:54])=[CH:52][CH:51]=2)[CH2:49][CH2:48][CH2:47][CH2:46]1.NC1C=CC=CC=1.NC1C=CC(OCCO)=CC=1.[N+](C1C=CC(OCCO)=CC=1)([O-])=O.[H][H]>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:54][C:53]4[CH:55]=[CH:56][C:50]([N:45]5[CH2:46][CH2:47][CH2:48][CH2:49]5)=[CH:51][CH:52]=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

11

Reactant 7

HCID 1176Urea2×HCID 6115Aniline2×HCID 808922-(4-Aminophenoxy)ethanolHCID 853812-(4-Nitrophenoxy)ethanolHCID 8088414-(Pyrrolidin-1-yl)anilineHCID 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-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 45488078HCID 45488078, 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 4-(1-pyrrolidinyl)-aniline as the aniline component. (41%, MS=539.3 (M+H))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-(4-aminophenoxy)ethanol (prepared by the reduction of 2-(4-nitrophenoxy)ethanol in ethyl acetate and methanol with palladium on carbon and hydrogen gas) as the aniline component. (2%, MS=530.4 (M+H))

Sources & evidence

ORD record
ord-93f55fbcf4ac4a4fae20f14bb5cf7de2
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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