5''-Bromo-[2,2';4',3'']terpyridin-6'-ylamine → 5''-[1-(Tetrahydro-pyran-4-yl)-1H-pyrazol-4-yl]-[2,2';4',3'']terpyridin-6'-ylamine

HRID 1798530Notes

Reaction equation

HRID 1798530 reaction equation
C[NH:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[C:5]([C:15]2[CH:16]=[N:17][CH:18]=[C:19](C3C=CC(C(N4CCN(C)CC4)=O)=CC=3)[CH:20]=2)[CH:4]=1.[O:36]1[CH2:41][CH2:40][CH:39]([N:42]2[CH:46]=[C:45](B3OC(C)(C)C(C)(C)O3)[CH:44]=[N:43]2)[CH2:38][CH2:37]1.BrC1C=C(C2C=C(N)N=C(C3C=CC=CN=3)C=2)C=NC=1>>[O:36]1[CH2:37][CH2:38][CH:39]([N:42]2[CH:46]=[C:45]([C:19]3[CH:20]=[C:15]([C:5]4[CH:4]=[C:3]([NH2:2])[N:8]=[C:7]([C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=5)[CH:6]=4)[CH:16]=[N:17][CH:18]=3)[CH:44]=[N:43]2)[CH2:40][CH2:41]1

Participants

4

Reactant 3

HCID 441360785''-Bromo-[2,2';4',3'']terpyridin-6'-ylamineHCID 44136079[4-(6'-Methylamino-[2,2';4',3'']terpyridin-5''-yl)-phenyl]-(4-methyl-piperazin-1-yl)-methanoneHCID 457884961-(Tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 687613825''-[1-(Tetrahydro-pyran-4-yl)-1H-pyrazol-4-yl]-[2,2';4',3'']terpyridin-6'-ylamine

Procedure

This compound is prepared analogously to [4-(6′-Methylamino-[2,2′;4′,3″]terpyridin-5″-yl)-phenyl]-(4-methyl-piperazin-1-yl)-methanone (Example 2.1) by replacing (4-methyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone with 1-(tetrahydro-pyran-4-yl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (Intermediate B18) and by replacing (5″-Bromo-[2,2′;4′,3″]terpyridin-6′-yl)-methyl-amine with 5″-Bromo-[2,2′;4′,3″]terpyridin-6′-ylamine (Example 1.31).

Sources & evidence

ORD record
ord-d409f41abd2a41bc86f0e7c9167e7988
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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