(2-Bromopyridin-4-yl)methanol → (2-(7-(4-Methylpyridin-3-yl)isoquinolin-3-ylamino)pyridin-4-yl)methanol

HRID 1502280Notes

Reaction equation

HRID 1502280 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]2)=[CH:10][CH:9]=1.Br[C:20]1[CH:25]=[C:24]([CH2:26][OH:27])[CH:23]=[CH:22][N:21]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([NH:18][C:20]3[CH:25]=[C:24]([CH2:26][OH:27])[CH:23]=[CH:22][N:21]=3)[N:14]=[CH:15]2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 14512957(2-Bromopyridin-4-yl)methanolHCID 679741997-(4-Methylpyridin-3-yl)isoquinolin-3-amine

Product 1

HCID 67974818(2-(7-(4-Methylpyridin-3-yl)isoquinolin-3-ylamino)pyridin-4-yl)methanolYield 44%

Procedure

The title compound was prepared following the procedures described for Example 13, using 7-(4-methylpyridin-3-yl)isoquinolin-3-amine and 2-bromopyridine-4-methanol, to yield 26.2 mg (44%) of (2-(7-(4-methylpyridin-3-yl)isoquinolin-3-ylamino)pyridin-4-yl)methanol. LCMS (ESI): RT (min)=2.759, M+H=343.1, method=E; 1H NMR (400 MHz, DMSO-d6) δ 9.79 (s, 1H), 9.12 (s, 1H), 8.57 (s, 1H), 8.49 (s, 1H), 8.47 (d, J=5.0 Hz, 1H), 8.23 (d, J=5.2 Hz, 1H), 8.00 (s, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.67 (d, J=8.6 Hz, 1H), 7.38 (d, J=4.9 Hz, 1H), 7.29 (s, 1H), 6.81 (d, J=5.1 Hz, 1H), 5.35 (t, J=5.7 Hz, 1H), 4.50 (d, J=5.6 Hz, 2H), 2.34 (s, 3H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-77613cf2df6741efb65640fc51bf69da
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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