Benzoyl chloride → HCID 46899293, compound

HRID 602789Notes

Reaction equation

HRID 602789 reaction equation
[C:1]1([S:7]([C:10]([CH:19]2[CH2:31][C:22]3[NH:23][C:24]4[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][C:29]=4[C:21]=3[CH2:20]2)([F:18])[C:11]2[O:15][N:14]=[C:13]([CH2:16][NH2:17])[N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[C:41](Cl)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1COCC1>[C:1]1([S:7]([C:10]([CH:19]2[CH2:31][C:22]3[NH:23][C:24]4[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][C:29]=4[C:21]=3[CH2:20]2)([F:18])[C:11]2[O:15][N:14]=[C:13]([CH2:16][NH:17][C:41](=[O:48])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[N:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 11453978HCID 11453978, compound

Product 1

HCID 46899293HCID 46899293, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 44 mg (0.095 mmol) of (RS,SR)-C-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-yl}-methylamine in 5 mL of THF, 19 μL (0.114 mmol, 1.2 eq) of Huenig's base and 11 μL (0.095 mmol, 1 eq) of benzoyl chloride were added at 0° C. After 2 hours, the reaction mixture was quenched by addition of an aqueous solution of NaHCO3 and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel EtOAc/Heptane 1:1 gave 28 mg (51%) of (RS,SR)-N-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-benzamide as a white solid, MS: 565 (M).

Workup

  1. customthe reaction mixture was quenched by addition of an aqueous solution of NaHCO3
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f2600a2788b44710bc14c30bca266914
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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