Cesium carbonate → HCID 89442703, compound

HRID 2284023Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[CH2:9][CH3:10].Cl.[N:12]1([CH2:16][CH2:17][N:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=3)[N:20]=[C:19]2[CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[N:12]1([CH2:16][CH2:17][N:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:28]=3)[N:20]=[C:19]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)[CH2:13][CH2:14][CH2:15]1

Participants

Conditions

Temperature: 120 °C

Procedure

A reaction mixture of 6-Chloro-5-ethyl-pyrimidin-4-ylamine (50.00 mg; 0.32 mmol; 1.00 eq.), 3-[1-(2-Azetidin-1-yl-ethyl)-2-piperidin-4-yl-1H-imidazol-4-yl]-5-trifluoromethyl-pyridine hydrochloride (3) (155.08 mg; 0.32 mmol; 1.00 eq.), and Cs2CO3 (206.74 mg; 0.63 mmol; 4.00 eq.) in DMSO 1.0 ml was stirred at 120° C. for 2 days, purified by HPLC, title compound 81 mg, 41.5%. LC-MS: (M+1=501, obsd.=501).

Workup

custompurified by HPLC, title compound 81 mg, 41.5%

Sources & evidence

ORD record: ord-3babceac75e347c98487d581c9c47191
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145392B2

Reaction notes

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