Cesium carbonate → HCID 178472575, compound

HRID 879531Notes

Reaction equation

Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[CH3:30][C:31]1[NH:32][C:33]2[CH2:38][CH2:37][NH:36][CH2:35][C:34]=2[N:39]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[C:25]([O:24][C@@H:18]([C:9]1[C:8]([CH3:29])=[CH:7][C:5]2[N:6]=[C:2]([N:36]3[CH2:37][CH2:38][C:33]4[NH:32][C:31]([CH3:30])=[N:39][C:34]=4[CH2:35]3)[S:3][C:4]=2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

A flask was charged with (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (100 mg, 0.20 mmol), 2-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine (85 mg, 0.40 mmol), Cs2CO3 (325 mg, 1.0 mmol), and then diluted with ACN (4 mL). The suspension was heated to 80° C. for 24 hours and then allowed to cool to room temperature. The resulting mixture was filtered and concentrated in vacuo. The crude residue was purified by reverse phase column chromatography (5-100% ACN/H2O+0.1% TFA)to afford the desired product. LCMS-ESI+: calc'd for C29H34ClN4O3S: 553.2 (M+H+); Found: 553.2 (M+H+).

Workup

temperatureto cool to room temperature
filtrationThe resulting mixture was filtered
concentrationconcentrated in vacuo
customThe crude residue was purified by reverse phase column chromatography (5-100% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record: ord-78dd4f189bce4851adf8be145984df7a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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