Quinoline-3-boronic acid → Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate

HRID 2047105Notes

Reaction equation

HRID 2047105 reaction equation
[CH3:1][Si:2]([CH3:48])([CH3:47])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4C([CH:26]=3)=CC=CC=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:32][CH2:31][CH:30]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:29][CH2:28]2)[CH:9]=1.C[N:50]1C=C(B2OC(C)(C)C(C)(C)O2)C=N1.N1C2C(=CC=CC=2)C=C(B(O)O)C=1>>[CH3:47][Si:2]([CH3:48])([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:26]=[N:50][N:19]([CH3:20])[CH:18]=3)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:28][CH2:29][CH:30]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:31][CH2:32]2)[CH:9]=1

Participants

4

Reactant 3

HCID 2734663Quinoline-3-boronic acidHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 66738318HCID 66738318, compound

Product 1

HCID 66734887Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate

Procedure

Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate was synthesized in a manner similar to the synthesis of ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate, but with N-methyl pyrazole-4-boronic acid pinacol ester substituted for quinoline-3-boronic acid.

Sources & evidence

ORD record
ord-31b9f3e4e3654e35a37529e1a5bdc6af
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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