1-Isobutyl-4-piperidone → HCID 86623562, compound

HRID 881480Notes

Reaction equation

HRID 881480 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][NH:12][CH3:13])=[CH:8][C:6]=2[N:7]=1.[CH3:20][CH:21]([CH3:30])[CH2:22][N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH:26]3[CH2:27][CH2:28][N:23]([CH2:22][CH:21]([CH3:30])[CH3:20])[CH2:24][CH2:25]3)[CH3:13])=[CH:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 42024511-Isobutyl-4-piperidoneHCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

Product 1

HCID 86623562HCID 86623562, compoundYield 48%

Procedure

(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methylamine was reacted with 1-(2-methylpropyl)-4-piperidone using standard reductive amination conditions. The resulting crude solid was triturated with diethyl ether and methanol to give (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-(1-isobutyl-piperidin-4-yl)-methyl-amine as a solid (48% yield), which was reacted with 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine according to General Procedure A. The resulting solid was triturated with diethylether and methanol to give 346 as a solid (60% yield). NMR (CDCl3, 400 MHz), 0.91 (6H, d, J=6.6), 1.587-1.70 (2H, m), 1.71-1.79 (3H, m), 1.89 (2H, t, J=11.7), 2.07 (2H, d, J=7.3), 2.37 (3H, s), 2.48-2.54 (1H, m), 2.96 (2H, d, J 11.6), 3.88-3.90 (4H, m), 3.93 (2H, s), 4.03-4.06 (4H, m), 5.22 (2H, br s), 7.27 (1H, s), 9.30 (2H, s). MS: (ESI+): MH+=497

Workup

  1. customThe resulting crude solid was triturated with diethyl ether and methanol

Sources & evidence

ORD record
ord-40e3f4a6b86347d9a3d777ddebcf4004
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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