Cesium carbonate → HCID 10460570, compound

HRID 900259Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-[2-(2-Methoxy-ethoxy)-ethoxymethyl]-3H-imidazole-4-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide (55 mg), 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole (46 mg), Cs2CO3 (98 mg), tetrabutylammonium iodide (8 mg) and DMF (3 mL) was stirred at 80° C. for 3 h. The solvent was removed in vacuo and the residue was taken up in DCM, washed with water, and the organic layer was dried over anhydrous MgSO4 and concentrated. The title compound (6 mg) was isolated after HPLC purification of the residue as its trifluoroacetate salt. MS (ESI+): m/e=566 [M+H]+, chloro pattern.

Workup

customThe solvent was removed in vacuo
washwashed with water
dry with materialthe organic layer was dried over anhydrous MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-79e12f47b45443dbaee1d651b977bf88
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358268B2

Reaction notes

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