Cesium carbonate → HCID 118290305, compound

HRID 57127Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[CH2:9][CH3:10].Cl.Cl.Cl.[N:14]1([CH2:18][CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=3)[N:22]=[C:21]2[CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[N:14]1([CH2:18][CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH3:32])[CH:26]=3)[N:22]=[C:21]2[CH:33]2[CH2:34][CH2:35][N:36]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=3[CH2:9][CH3:10])[CH2:37][CH2:38]2)[CH2:15][CH2:16][CH2:17]1

Participants

Conditions

Temperature: 120 °C

Procedure

The reaction mixture of 6-chloro-5-ethyl-pyrimidin-4-ylamine (30.0 mg; 0.19 mmol; 1.0 eq.), 4-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidine trihydrochloride (86.0 mg; 0.19 mmol; 1.0 eq.), and Cs2CO3 (310.1 mg; 0.95 mmol; 5.0 eq.) in DMSO (1.5 ml) was stirred at 120° C. for 48 hr. The crude was purified by prep HPLC to afford the title compound. LC-MS (M+H=464, obsd=464). 1H NMR (400 MHz, DMSO-d6) δ 8.49-8.39 (m, 1H), 8.10-8.01 (m, 1H), 7.96 (s, 1H), 7.93-7.85 (m, 1H), 7.50 (t, J=8.9 Hz, 1H), 6.69-6.61 (m, 2H), 4.30 (q, J=5.4, 4.7 Hz, 2H), 2.71-2.62 (m, 2H), 3.93 (d, J=12.5 Hz, 2H), 3.54 (q, J=6.3, 5.8 Hz, 4H), 3.33 (t, J=12.5 Hz, 3H), 3.11 (q, J=5.3, 4.0 Hz, 2H), 2.33 (dd, J=28.0, 11.5 Hz, 6H), 1.54 (q, J=6.7, 6.0 Hz, 3H).

Workup

customThe crude was purified by prep HPLC

Sources & evidence

ORD record: ord-f3b4df42b2f64018aba19d66fdbdcd20
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434714B2

Reaction notes

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