Potassium Carbonate → 4-[3-(4-Trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid methyl ester

HRID 1172212Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane (60 mg, 0.21 mmol), 4-chlorosulfonyl-indan-2(R,S)-carboxylic acid methyl ester (120 mg, 0.44 mmol), potassium carbonate (200 mg, 1.4 mmol), and acetonitrile (3 mL) were heated at 50° C. for 2 h. The mixture was filtered through Celite, concentrated, and purified by silica gel chromatography (9:1→4:1; hexanes:ethyl acetate) to give 4-[3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid methyl ester: MS (ESI): 525.5 (M+H).

Workup

filtrationThe mixture was filtered through Celite
concentrationconcentrated
custompurified by silica gel chromatography (9:1→4:1; hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-4dbb1001eb704658a8e917968bd08d34
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834004B2

Reaction notes

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