Propylamine → HCID 57496303, compound

HRID 1864145Notes

Reaction equation

[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]3[N:20]([C:23]4[CH:28]=[CH:27][C:26](I)=[CH:25][C:24]=4[CH3:30])[N:21]=[CH:22][C:15]=23)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH2:31]([NH2:34])[CH2:32][CH3:33].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu](I)I>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]3[N:20]([C:23]4[CH:28]=[CH:27][C:26]([NH:34][CH2:31][CH2:32][CH3:33])=[CH:25][C:24]=4[CH3:30])[N:21]=[CH:22][C:15]=23)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

4-[1-(4-Iodo-2-methyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (78 mg, 0.15 mmol), propyl amine (0.75 mmole, 5 eq), proline (0.27 mole, 1.8 eq), copper iodide (0.15 mmole, 1 eq), and potassium carbonate (0.15 mmole, 1 eq) were dissolved in DMSO (2 mL) and then stirred at 100° C. for 30 mins in microwave. The crude was purified through Prep-TLC (Hexane:Ethyl Acetate=1:1, Rf=0.7) to provid compound A215 as white solid (36 mg, 53%). 1H NMR 400MHz CDCl3 δ (ppm): 8.51 (s, 1H); 8.20 (s, 1H); 7.40-7.36 (m, 1H); 7.30-7.21 (m, 2H); 5.63-5.58 (m, 1H); 4.95 (sep, 1H); 3.89 (m, 2H); 3.41-3.35 (m, 2H); 3.23-3.19 (m, 2H); 2.16-2.03 (m, 4H); 1.89-1.86 (m, 2H); 1.27 (d, 6H); 1.04 (t, 2H). Exact mass calculated for C24H32N6O3 452.2, found LCMS (ESI) m/z 453.4 (M+H+, 100%).

Workup

customThe crude was purified through Prep-TLC (Hexane:Ethyl Acetate=1:1, Rf=0.7)
customto provid compound

Sources & evidence

ORD record: ord-89b5d6752bd549e88b373072afe5a3c0
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625906B2

Reaction notes

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