Cyanogen Bromide → 5-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amine

HRID 1949837Notes

Reaction equation

HRID 1949837 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15](=[N:24][NH2:25])[NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[Cl:23])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1.[N:27]#[C:28]Br>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]4[N:16]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=5[Cl:23])[C:28]([NH2:27])=[N:25][N:24]=4)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 178514378HCID 178514378, compound

Product 1

HCID 579002025-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amineYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of crude 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbohydrazonamide (195, 0.434) in methanol (5 mL) was treated with a solution of cyanogen bromide (115 mg, 1.1 mmol) in methanol (1 mL) at room temperature. The reaction vessel was sealed and heated at 45° C. for 2 h, cooled to room temperature, quenched upon addition of saturated sodium bicarbonate and extracted with ethylacetate. The combined organics were dried over sodium sulfate and concentrated and the residue purified by flash column chromatography (1-10% MeOH in methylene chloride to give 287 (43 mg, 21% yield). MS (ESI): 475.0

Workup

  1. customThe reaction vessel was sealed
  2. temperaturecooled to room temperature
  3. customquenched upon addition of saturated sodium bicarbonate
  4. extractionextracted with ethylacetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue purified by flash column chromatography (1-10% MeOH in methylene chloride

Sources & evidence

ORD record
ord-b6606eb7c9b74605b9fb8a6706aec9b7
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

Loading…