Formamide → HCID 44242297, compound

HRID 84436Notes

Reaction equation

HRID 84436 reaction equation
[N:1]1[C:11]2[C:10]3[S:12][C:13]([CH:15](Br)[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])=[O:17])=[CH:14][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:26]([NH2:28])=O>O>[N:1]1[C:11]2[C:10]3[S:12][C:13]([C:15]4[N:28]=[CH:26][O:17][C:16]=4[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])=[CH:14][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 866348406,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl-(2-chlorophenyl)-2-bromoethanone

Product 1

HCID 44242297HCID 44242297, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6,7-Dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl-(2-chlorophenyl)-2-bromoethanone from Example 37 (65.0 mg, 0.150 mmol) was suspended in formamide (2 mL, 50 mmol). The reaction was microwaved on 300 watts at 130° C. for 20 minutes. Water was added and the product was extracted with ethylacetate. The organic layer was washed with water twice and brine, dried over MgSO4, and evaporated to dryness. The crude product was purified on silica gel column, eluting with 25% of ethylacetate in hexane to give 129 (yield 10 mg, 18%). MS (ESI+) 381.1

Workup

  1. customThe reaction was microwaved on 300 watts at 130° C. for 20 minutes
  2. extractionthe product was extracted with ethylacetate
  3. washThe organic layer was washed with water twice
  4. dry with materialbrine, dried over MgSO4
  5. customevaporated to dryness
  6. customThe crude product was purified on silica gel column
  7. washeluting with 25% of ethylacetate in hexane

Sources & evidence

ORD record
ord-1fa07aa3ddba4b31ac2e5c95f165c48a
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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