Urea → 1-(4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)-3-(4-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)urea

HRID 1093282Notes

Reaction equation

HRID 1093282 reaction equation
NC(N)=O.[CH:5]12[O:12][CH:9](CC1)[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.[CH3:45][N:46]([CH3:58])[CH2:47][CH2:48][N:49]([CH3:57])[C:50]1[CH:55]=[CH:54][C:53]([NH2:56])=[CH:52][CH:51]=1.N[C:60]1C=CC=C[CH:61]=1>>[CH:8]12[N:7]([C:13]3[N:18]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]([NH:25][C:26]([NH:56][C:53]5[CH:54]=[CH:55][C:50]([N:49]([CH2:48][CH2:47][N:46]([CH3:58])[CH3:45])[CH3:57])=[CH:51][CH:52]=5)=[O:27])=[CH:23][CH:24]=4)[N:16]=[C:15]4[N:31]([CH2:34][CH3:35])[N:32]=[CH:33][C:14]=34)[CH:6]([CH2:60][CH2:61]1)[CH2:5][O:12][CH2:9]2

Participants

5

Reactant 4

HCID 1176UreaHCID 6115AnilineHCID 21873395N-(2-Dimethylaminoethyl)-N-methylbenzene-1,4-diamineHCID 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-carboxylate

Product 1

HCID 574246871-(4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)-3-(4-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)urea

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 N1-(2-(dimethylamino)ethyl)-N1-methylbenzene-1,4-diamine as the aniline component. (40%, MS=570.5 (M+H))

Sources & evidence

ORD record
ord-c2632c849d5b432b85d1a902b2a990cf
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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