4-Acetamidopiperidine → Diisopropylethylamine

HRID 1409260Notes

Reaction equation

HRID 1409260 reaction equation
ClC1N2N=C(C)C=C2N=C(NC(=O)[C:14]2C=[CH:18][C:17]([C:20](O)(C)C)=[N:16][CH:15]=2)C=1.N1CC[CH:28](NC(=O)C)[CH2:27][CH2:26]1>CN1C(=O)CCC1>[CH:27]([N:16]([CH2:15][CH3:14])[CH:17]([CH3:18])[CH3:20])([CH3:28])[CH3:26]

Participants

4

Reactant 2

HCID 14451564-AcetamidopiperidineHCID 86652280HCID 86652280, compound

Product 1

HCID 81531DiisopropylethylamineYield 114.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 2 ml microwave vial was placed N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-6-(2-hydroxypropan-2-yl)nicotinamide (11C, 75 mg, 0.21 mmol) and N-(piperidin-4-yl)acetamide (31 mg, 0.21 mmol). To the sealed vial was then added NMP (1 ml) and then N,N-diisopropylethylamine (0.042 ml, 0.24 mmol) to give a dark yellow solution. The mixture was then heated in the microwave at 100° C. for 10 minutes. After cooling to room temperature, the crude product mixture was purified by preparatory HPLC (20-40% MeCN/H2O gradient+0.01% TFA). Lyophilization of the collected fractions gave the titled product (77 mg, 79% yield) as an off white powder. 1H NMR (DMSO-d6) δ: 11.07 (s, 1H), 9.00 (dd, J=2.4, 0.9 Hz, 1H), 8.33 (dd, J=8.3, 2.3 Hz, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.75 (dd, J=8.3, 0.8 Hz, 1H), 7.26 (s, 1H), 6.11 (d, J=0.5 Hz, 1H), 4.28 (br. s., 2H), 3.76-3.90 (m, 2H), 3.11-3.21 (m, 2H), 2.32 (s, 4H), 1.80-1.90 (m, 3H), 1.76 (s, 3H), 1.51 (d, J=8.8 Hz, 3H), 1.41 (s, 6H); ESI-MS: m/z 452.3 (M+H)+.

Sources & evidence

ORD record
ord-9565bbf928894b93ba06bdba763e1912
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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