1-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)piperazine → 5''-(3-Aminomethyl-5-methyl-phenyl)-[2,2';4',3'']terpyridin-6'-ylamine

HRID 1798531Notes

Reaction equation

HRID 1798531 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[C:4]([C:14]2[CH:15]=[N:16][CH:17]=[C:18](C3C=CC(C(N4CCNCC4)=O)=CC=3)[CH:19]=2)[CH:3]=1.N1(C(C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)=O)CCNCC1.[NH2:57][CH2:58][C:59]1[CH:60]=[C:61](B(O)O)[CH:62]=[C:63]([CH3:65])[CH:64]=1>>[NH2:57][CH2:58][C:59]1[CH:60]=[C:61]([C:18]2[CH:19]=[C:14]([C:4]3[CH:3]=[C:2]([NH2:1])[N:7]=[C:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=4)[CH:5]=3)[CH:15]=[N:16][CH:17]=2)[CH:62]=[C:63]([CH3:65])[CH:64]=1

Participants

4

Reactant 3

HCID 177499131-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)piperazineHCID 44137101[4-(6'-Amino-[2,2';4',3'']terpyridin-5''-yl)-phenyl]-piperazin-1-yl-methanoneHCID 866336493-Aminomethyl-5-methyl-phenyl boronic acid

Product 1

HCID 687352655''-(3-Aminomethyl-5-methyl-phenyl)-[2,2';4',3'']terpyridin-6'-ylamine

Procedure

This compound is prepared analogously to [4-(6′-Amino-[2,2′;4′,3″]terpyridin-5″-yl)-phenyl]-piperazin-1-yl-methanone (Example 2.50) by replacing piperazin-1-yl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone with 5″-(3-Aminomethyl-5-methyl-phenyl boronic acid (Intermediate B27).

Sources & evidence

ORD record
ord-eae63a1f715749e19292d3e200fdc41b
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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