HCID 59769935, compound → HCID 9982242, compound

HRID 2218772Notes

Reaction equation

HRID 2218772 reaction equation
Br/[CH:2]=[C:3]1/[C:4]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:5]=2[O:6][CH2:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]/1=2.[N:19]1([CH2:25][CH2:26][N:27]2[C:31]3[CH:32]=[CH:33][C:34](C4(O)CCCB4O)=[CH:35][C:30]=3[NH:29][C:28]2=[O:43])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>>[F:18][C:15]1[CH:16]=[CH:17][C:4]2=[C:5]([CH:14]=1)[O:6][CH2:7][C:8]1[N:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[C:3]/2=[CH:2]\[C:34]1[CH:33]=[CH:32][C:31]2[N:27]([CH2:26][CH2:25][N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:28](=[O:43])[NH:29][C:30]=2[CH:35]=1

Participants

3

Reactant 2

HCID 59769935HCID 59769935, compoundHCID 86631076HCID 86631076, compound

Product 1

HCID 9982242HCID 9982242, compoundYield 39%

Procedure

Following procedures essentially as described in Example 219, beginning with (E)-5-bromomethylene-8-fluoro-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cycloheptene (192 mg, 0.63 mmol) and 1-(2-morpholinyl-ethyl)-5-(dihyroxyborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (219 mg, 0.75 mmol). Partition the reaction mixture between ethyl acetate (50 mL) and 1N aqueous hydrochloric acid solution (50 mL). Separate the layers and extract the aqueous layer with methylene chloride (2×50 mL). Combine the organic layers and extract with 1N aqueous hydrochloric acid solution (50 mL). Adjust the pH of the combined aqueous layers to 8.0 with 5N aqueous sodium hydroxide solution, and extract the product with ethyl acetate (3×50 mL). Purify the crude product by flash chromatography (25% ethanol/ethyl acetate) to provide 115 mg (39%) of purified product.

Workup

  1. customPartition the reaction mixture between ethyl acetate (50 mL) and 1N aqueous hydrochloric acid solution (50 mL)
  2. customSeparate the layers
  3. extractionextract the aqueous layer with methylene chloride (2×50 mL)
  4. extractionCombine the organic layers and extract with 1N aqueous hydrochloric acid solution (50 mL)
  5. extractionextract the product with ethyl acetate (3×50 mL)
  6. customPurify the crude product by flash chromatography (25% ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-f73f3cb30fee4587b34cc6aca4112bf8
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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