Sodium Iodide → HCID 68595616, compound

HRID 341186Notes

Reaction equation

[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14]([C:17]4[CH:18]=[C:19]([NH:23][C:24]([NH:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[O:25])[CH:20]=[CH:21][CH:22]=4)=[CH:15][N:16]=[C:10]3[CH:9]=2)[CH:4]=[CH:3]1.Cl.[Cl:33][CH2:34][CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-]>CN(C=O)C>[ClH:33].[O:1]=[C:2]1[N:7]([CH2:34][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14]([C:17]4[CH:18]=[C:19]([NH:23][C:24]([NH:26][CH2:27][C:28]([F:29])([F:30])[F:31])=[O:25])[CH:20]=[CH:21][CH:22]=4)=[CH:15][N:16]=[C:10]3[CH:9]=2)[CH:4]=[CH:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 1-{3-[7-(6-Oxo-1,6-dihydro-pyridin-3-yl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea (0.12 g, 0.63 mmol) in DMF (1.5 ml) was added N-(3-chloropropyl)piperidine hydrochloride (0.125 g, 0.63 mmol), Cs2CO3 (0.32 g, 0.98 mmol) and NaI (0.095 g, 0.63 mmol). The reaction was heated at 80° C. for 48 hours then partitioned between EtOAc and water, the organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (16 mg) MS: [M+H]+553

Workup

customthen partitioned between EtOAc and water
washthe organic layer was washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-8bfcb7b649bd46aa8f8b6483788fcc42
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895745B2

Reaction notes

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