Cesium carbonate → HCID 58154649, compound

HRID 2359396Notes

Reaction equation

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

Participants

Conditions

Temperature: 200 °C

Procedure

A solution of N-(2-(2-hydroxyphenyl)quinolin-8-yl)thiazole-4-carboxamide (0.1 g, 0.287 mmol), 4-(2-chloroethyl)morpholine (0.129 g, 0.862 mmol), and cesium carbonate (0.7 g, 2.15 mmol) in DMF (5 mL) was microwave heated (200° C.×2 hours). The crude material was filtered and purified by silica gel chromatography (gradient of 0 to 90% ethyl acetate in pentane). MS (ESI) calcd for C25H24N4O3S (m/z): 460.16. found: 461 [M+1].

Workup

filtrationThe crude material was filtered
custompurified by silica gel chromatography (gradient of 0 to 90% ethyl acetate in pentane)

Sources & evidence

ORD record: ord-fba308dcea774b15a4770b7aa285b168
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685970B2

Reaction notes

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