N-methyl-2-pyrrolidone → Diisopropylethylamine
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.CN1C(=O)[CH2:29][CH2:28][CH2:27]1>>[CH:28]([N:16]([CH2:15][CH3:14])[CH:17]([CH3:18])[CH3:20])([CH3:29])[CH3:27]Participants
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, 0.217 mmol) and 1-(piperidin-4-yl)urea, HCl salt (39 mg, 0.22 mmol). To the sealed vial was then added NMP (1 ml) and then N,N-diisopropylethylamine (0.079 ml, 0.46 mmol) to give a deep blue 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 (47 mg, 48% yield) as an off white powder. 1H NMR (DMSO-d6) δ: 11.13 (s, 1H), 9.07 (dd, J=2.4, 0.9 Hz, 1H), 8.38 (dd, J=8.3, 2.3 Hz, 1H), 7.80 (d, J=8.3 Hz, 1H), 7.33 (s, 1H), 6.17 (d, J=0.5 Hz, 1H), 6.06-6.15 (m, 1H), 4.31 (d, J=12.6 Hz, 2H), 3.69 (br. s., 1H), 3.22 (t, J=10.9 Hz, 2H), 2.38 (s, 3H), 1.90-1.99 (m, 2H), 1.51 (br. s., 2H), 1.47 (s, 7H); ESI-MS: m/z 453.3 (M+H)+.
Sources & evidence
- ORD record
- ord-b0607644c5b0479580800c70cfff52f0
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921358B2
Reaction notes
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