Potassium Carbonate → HCID 11655664, compound

HRID 1626219Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:7][C:6]=1[C:21]1[N:22]([CH3:26])[N:23]=[CH:24][CH:25]=1.[C:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:27]([N:30]1[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[CH:7][C:6]=2[C:21]2[N:22]([CH3:26])[N:23]=[CH:24][CH:25]=2)[CH2:32][CH2:31]1)(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-[4-(2-Bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-3-fluoro-benzamide (105 mg, 0.251 mmol), 1-acetylpiperazine (34 mg, 0.264 mmol) and potassium carbonate (42 mg, 0.301 mmol) in DMF (3 mL) was heated in microwave at 120° C. for 20 min. The mixture was purified by HPLC to give title compound (75 mg, 64%) as a white solid as TFA salt. 1H NMR (CD3CN, 400 MHz) δ 2.09 (s, 3H), 3.32-3.38 (m, 6H), 3.48 (t, J=5.05 Hz, 4H), 3.79 (s, 3H), 4.43 (t, J=4.55 Hz, 2H), 6.39 (d, J=2.02 Hz, 1H), 7.18 (d, J=9.09 Hz, 1H), 7.40 (dt, J=2.78, 8.59 Hz, 1H), 7.57-7.63 (m, 2H), 7.70-7.74 (m, 2H), 7.80-7.82 (m, 1H), 7.85 (dd, J=2.78, 9.09 Hz, 1H), 8.93 (s, 1H). Exact mass calculated for C25H28FN5O3 465.2, found 466.4 (MH+).

Workup

customThe mixture was purified by HPLC

Sources & evidence

ORD record: ord-db19c2bb8ee541c8ad506d65f53e65a0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785441B2

Reaction notes

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