Water → HCID 58392320, compound

HRID 561606Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9](O)([CH3:13])[CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.[Cl-].[In+3].[Cl-].[Cl-].[CH3:21][S:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[CH:29]2.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:21][S:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[NH:31][CH:30]=[C:29]2[C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:4][CH:5]=1)([CH3:13])[CH2:10][CH2:11][OH:12]

Participants

Conditions

Temperature: 80 °C

Procedure

1.59 g (91% purity, approx. 6.77 mmol) of the compound from Example 89A and 1.50 g (6.77 mmol) of indium(III) chloride were added to 1.20 g (6.77 mmol) of the compound from Example 8A in 29 ml of toluene. The reaction mixture was stirred at 80° C. for 5 h. After cooling to RT, the reaction solution was mixed with water and ethyl acetate, and the solid was filtered off. The phases of the filtrate were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 0.14 g (5% of theory) of the title compound.

Workup

temperatureAfter cooling to RT
filtrationthe solid was filtered off
customThe phases of the filtrate were separated
extractionthe aqueous phase was extracted with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-6f4cb5bfefbe4154b92d0345452de9f4
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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