4-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-2H-benzo[B][1,4]oxazin-3(4H)-one → 6-(2-(2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl)-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 2090476Notes

Reaction equation

HRID 2090476 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH3:26])[N:8]([C:12]3[CH:17]=[C:16]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[N:15]=[C:14]([NH2:25])[N:13]=3)[CH2:9]2)=[CH:4][CH:3]=1.[CH3:27][N:28]1[C:33]2[CH:34]=[C:35](B3OC(C)(C)C(C)(C)O3)[CH:36]=[CH:37][C:32]=2[O:31][CH2:30][C:29]1=[O:47]>>[NH2:25][C:14]1[N:13]=[C:12]([N:8]2[CH:7]([CH3:26])[CH2:6][C:5]3[C:10](=[CH:11][C:2]([C:35]4[CH:36]=[CH:37][C:32]5[O:31][CH2:30][C:29](=[O:47])[N:28]([CH3:27])[C:33]=5[CH:34]=4)=[CH:3][CH:4]=3)[CH2:9]2)[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[N:15]=1

Participants

3

Reactant 2

HCID 532172054-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-2H-benzo[B][1,4]oxazin-3(4H)-oneHCID 594023174-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

Product 1

HCID 594022746-(2-(2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl)-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 129, Step 4 starting from 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine and 4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-1,4-benzoxazin-3(4H)-one. LCMS (M+H)+: m/z=500.2.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-a71201f9992d44cda350488396e2ceb2
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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