Potassium Carbonate → HCID 118290344, compound

HRID 57130Notes

Reaction equation

[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=3)[N:9]=[C:8]2[CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH2:4][CH2:3][CH2:2]1.Cl[C:27]1[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:28]=1[CH:34]([CH3:36])[CH3:35].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N:1]1([CH2:5][CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=3)[N:9]=[C:8]2[CH:20]2[CH2:21][CH2:22][N:23]([C:27]3[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:28]=3[CH:34]([CH3:36])[CH3:35])[CH2:24][CH2:25]2)[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: 120 °C

Procedure

The mixture of 4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidine (162.8 mg; 0.47 mmol; 1.0 eq.), 6-chloro-5-isopropyl-pyrimidin-4-ylamine (81.6 mg; 0.47 mmol; 1.0 eq.) and potassium carbonate (82.1 m g; 0.59 mmol; 1.25 eq.) in DMSO (3 ml) was stirred 120° C. for 56 hr. The crude was purified by prep HPLC to afford the title compound. LC-MS (M+H=478, obsd=478). 1H NMR (400 MHz, DMSO-d6) δ 8.02 (s, 1H), 7.66-7.59 (m, 1H), 7.54 (ddd, J=7.7, 4.9, 2.1 Hz, 1H), 7.48 (s, 1H), 7.08 (t, J=9.1 Hz, 1H), 6.13 (s, 2H), 3.87 (t, J=6.2 Hz, 2H), 3.11 (t, J=6.9 Hz, 4H), 2.93-2.80 (m, 3H), 2.68 (t, J=6.2 Hz, 2H), 2.30-2.21 (m, 3H), 1.92 (dtd, J=24.6, 12.8, 12.1, 4.0 Hz, 5H), 1.30 (d, J=7.2 Hz, 6H).

Workup

customThe crude was purified by prep HPLC

Sources & evidence

ORD record: ord-8ed12f7fe0954c2ea3d59f5a1c37d109
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434714B2

Reaction notes

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