6-Bromo-4H-imidazo[4,5-b]pyridine → 4-[7-(3H-Imidazo[4,5-b]pyridin-6-yl)-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

HRID 2090479Notes

Reaction equation

HRID 2090479 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([N:14]3[CH:23]([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][C:18](B5OC(C)(C)C(C)(C)O5)=[CH:19][CH:20]=4)[CH2:15]3)[N:11]=[C:10]([NH2:34])[N:9]=2)[CH2:4][CH2:3]1.Br[C:36]1[CH:37]=[C:38]2[N:44]=[CH:43][NH:42][C:39]2=[N:40][CH:41]=1>>[N:44]1[C:38]2[C:39](=[N:40][CH:41]=[C:36]([C:18]3[CH:17]=[C:16]4[C:21]([CH2:22][CH:23]([CH3:24])[N:14]([C:12]5[CH:13]=[C:8]([N:5]6[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]6)[N:9]=[C:10]([NH2:34])[N:11]=5)[CH2:15]4)=[CH:20][CH:19]=3)[CH:37]=2)[NH:42][CH:43]=1

Participants

3

Reactant 2

HCID 9115786-Bromo-4H-imidazo[4,5-b]pyridineHCID 594022564-(4-methylpiperazin-1-yl)-6-[3-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl]pyrimidin-2-amine

Product 1

HCID 1784218964-[7-(3H-Imidazo[4,5-b]pyridin-6-yl)-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 116 starting from 4-(4-methylpiperazin-1-yl)-6-[3-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl]pyrimidin-2-amine (Example 116, Step 1) and 6-bromo-3H-imidazo[4,5-b]pyridine (Focus synthesis, Cat. No. FS000626). LCMS (M+H)+: m/z=456.2.

Workup

  1. customThis compound was prepared
  2. customFocus synthesis, Cat

Sources & evidence

ORD record
ord-d22b11552a7b4bf1967d5a11acc22655
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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