Ethyl orthoformate → HCID 57900205, compound

HRID 628023Notes

Reaction equation

HRID 628023 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:12]1[S:25][C:15]2[C:16]3[CH:24]=[N:23][CH:22]=[CH:21][C:17]=3[O:18][CH2:19][CH2:20][C:14]=2[CH:13]=1)=[N:10][NH2:11].[CH2:26](OC(OCC)OCC)C>>[S:25]1[C:15]2[C:16]3[CH:24]=[N:23][CH:22]=[CH:21][C:17]=3[O:18][CH2:19][CH2:20][C:14]=2[CH:13]=[C:12]1[C:9]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:26]=[N:11][N:10]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 178514379N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine-2-carbohydrazonamide

Product 1

HCID 57900205HCID 57900205, compoundYield 38%

Conditions

Temperature
85 °C

Procedure

A mixture of N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine-2-carbohydrazonamide (44 mg, 0.12 mmol) and 3 ml of triethylorthoformate was heated at 85° C. for 4 hours. The mixture was concentrated in vacuum and triturated with diethylether. The precipitate was collected, washed with diethylether and purified by flash chromatography eluting with 60% of ethyl acetate in hexane to give 320 (17 mg, 38%). MS: (ESI+) 381.1

Workup

  1. concentrationThe mixture was concentrated in vacuum
  2. customtriturated with diethylether
  3. customThe precipitate was collected
  4. washwashed with diethylether
  5. custompurified by flash chromatography
  6. washeluting with 60% of ethyl acetate in hexane

Sources & evidence

ORD record
ord-941b7e8012724a23bc85b74817be042d
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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