Potassium Carbonate → HCID 58964316, compound

HRID 1626176Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:7][C:6]=1[C:18]1[N:19]([CH3:23])[N:20]=[CH:21][CH:22]=1.[OH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[OH:24][CH:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:7][C:6]=2[C:18]2[N:19]([CH3:23])[N:20]=[CH:21][CH:22]=2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of pentanoic acid [4-(2-chloro-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-amide (50 mg, 0.15 mmol), 4-hydroxypiperidine (18 mg, 0.18 mmol), potassium carbonate (31 mg, 0.225 mmol) and catalytic amount of tetrabutyl ammonium iodide in DMF (1 mL) was heated with microwaves at 100° C. for 2.5 hours. The crude was purified by HPLC to provide the title compound as a sticky solid (51 mg, 85%). 1H NMR (DMSO-d6, 400 MHz) δ 0.89 (t, J=7.33 Hz, 3H), 1.30 (guar, J=7.58 Hz, 2H), 1.40-1.48 (m, 1H), 1.54 (quin, J=7.58 Hz, 2H), 1.66-1.82 (m, 2H), 2.28 (t, J=7.33 Hz, 2H), 2.82-2.89 (m, 1H), 3.05-3.09 (m, 2H), 3.19-3.22 (m, 1H), 3.39-3.45 (m, 2H), 3.64 (d, J=2.53 Hz, 3H), 3.85 (s, 1H), 4.11-4.18 (m, 4H), 6.25 (dd, J=2.02, 5.05 Hz, 1H), 7.16 (d, J=9.09 Hz, 1H), 7.45 (dd, J=2.02, 5.31 Hz, 1H), 7.55 (d, J=2.78 Hz, 1H), 7.66 (dd, J=2.53, 9.09 Hz, 1H), 9.23 (s, br, 1H), 9.91 (s, 1H). Exact mass calculated for C22H32N4O3 400.2, found 401.3 (MH+).

Workup

customThe crude was purified by HPLC

Sources & evidence

ORD record: ord-ccc9c1a90e234ef097350f4b2be03975
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785441B2

Reaction notes

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