2-(1-((2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol → 2-(1-((2-(1-(Ethylamino)isoquinolin-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

HRID 1945727Notes

Reaction equation

HRID 1945727 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([C:18]([OH:21])([CH3:20])[CH3:19])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.Br[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([NH:39][CH2:40][CH3:41])=[N:31][CH:30]=1>>[CH2:40]([NH:39][C:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:29]([C:2]2[N:3]=[C:4]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:17][CH2:16][CH:15]([C:18]([OH:21])([CH3:20])[CH3:19])[CH2:14][CH2:13]4)=[CH:8][C:6]=3[N:7]=2)=[CH:30][N:31]=1)[CH3:41]

Participants

3

Reactant 2

HCID 574940322-(1-((2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-olHCID 596052034-bromo-N-ethylisoquinolin-1-amine

Product 1

HCID 596055302-(1-((2-(1-(Ethylamino)isoquinolin-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Procedure

Following the procedures for 108, 2-(1-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol and 4-bromo-N-ethylisoquinolin-1-amine were converted to 137. LCMS: M+H+=547. 1H NMR (400 MHz, DMSO) δ 9.03 (d, J=8.5, 1H), 8.67 (s, 1H), 8.28 (d, J=8.3, 1H), 7.68 (dd, J=16.9, 6.5, 2H), 7.51 (t, J=7.5, 1H), 7.37 (s, 1H), 4.04 (s, 1H), 3.93 (d, J=4.8, 4H), 3.80 (d, J=6.3, 6H), 3.65-3.54 (m, 2H), 2.99 (d, J=10.9, 2H), 2.07 (s, 1H), 1.97 (t, J=11.5, 2H), 1.67 (d, J=10.9, 2H), 1.36-1.12 (m, 6H), 1.04 (s, 6H)

Sources & evidence

ORD record
ord-5c91ffb6e6ec4fb5a7ef9b6a6a9a06ce
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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