Dimethylformamide → HCID 58205026, compound

HRID 1498084Notes

Reaction equation

HRID 1498084 reaction equation
I[C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[C:12]([C:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=3[O:8][CH2:7][CH2:6][N:5]2[CH:18]=1.[Cu](C#N)[C:20]#[N:21].[CH3:24]N(C)C=O>>[C:20]([C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[C:12]([C:15]([O:17][CH3:24])=[O:16])[CH:13]=[CH:14][C:9]=3[O:8][CH2:7][CH2:6][N:5]2[CH:18]=1)#[N:21]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 86652297HCID 86652297, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 58205026HCID 58205026, compoundYield 81%

Procedure

2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylate (370.1 mg, 1.0 mmol) and Copper cyanide (268.6 mg, 3.000 mmol) were mixed in 8 ml of N,N-Dimethylformamide. The reaction was microwaved on 200 watts, 150° C., for 40 minutes. The reaction mixture was partitioned between 25 ml of 5% ammonia in water and 25 ml of EtOAc. The aqueous layer was additionally extracted with 3×20 ml EtOAc, combined extracts were washed with water, brine and dried over MgSO4 to afford 225 mg of methyl 2-cyano-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylate. Yield 81%. (MS: 270.0).

Workup

  1. customThe reaction was microwaved on 200 watts, 150° C., for 40 minutes
  2. customThe reaction mixture was partitioned between 25 ml of 5% ammonia in water and 25 ml of EtOAc
  3. extractionThe aqueous layer was additionally extracted with 3×20 ml EtOAc
  4. washwere washed with water, brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-44c20687465f49f2af2bc24d60140154
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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