Acetic Anhydride → HCID 68717514, compound

HRID 229623Notes

Reaction equation

HRID 229623 reaction equation
NC1C2=C(C3C=CC([N+]([O-])=O)=CC=3)C(C=O)=CN2N=CN=1.Cl.NO.C(OC(=O)C)(=O)C.[C:32]([C:34]1[C:35]([C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[C:36]2[N:41]([CH:42]=1)[N:40]=[CH:39][N:38]=[C:37]2[NH:43]C(=O)C)#[N:33]>CCOC(C)=O.O.N1C=CC=CC=1>[NH2:43][C:37]1[C:36]2=[C:35]([C:47]3[CH:48]=[CH:49][C:50]([N+:53]([O-:55])=[O:54])=[CH:51][CH:52]=3)[C:34]([C:32]#[N:33])=[CH:42][N:41]2[N:40]=[CH:39][N:38]=1

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 57757971HCID 57757971, compound2×HCID 68713612HCID 68713612, compound

Product 1

HCID 68717514HCID 68717514, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of pyridine (8.75 mL) was added 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carbaldehyde (Intermediate H, Step 2) (500 mg, 1.77 mmol) followed by hydroxylamine hydrochloride (135 mg, 1.94 mmol). The solution was stirred at rt for 1 h, acetic anhydride (366 mL, 3.88 mmol) was added, and the solution was heated to 80° C. for 17 h. Upon cooling to rt the reaction mixture was partially rotavapped and then diluted with EtOAc (50 mL) and H2O (50 mL). The solution was transferred to a separatory funnel, and the organic layer was isolated while the aqueous layers were back extracted with EtOAc (2×25 mL). The combined organic layers were collected, dried (Na2SO4), filtered, and concentrated to dryness to afford a brown solid. This proved to be a 1:1 ratio of the title compound and N-[6-cyano-5-(4-nitro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-yl]-acetamide. 1H-NMR (DMSO-d6) δ 10.67 (s, 1H), 8.96 (s, 1H), 8.62 (s, 1H), 8.57(s, 1H), 8.40 to 8.30 (m, 4H), 8.05 (s, 1H), 7.79 to 7.68 (m, 4H), 1.74 (s, 3H); MS [M+H]+=281.2, 323.0; LCMS RT=2.48 min.

Workup

  1. temperaturethe solution was heated to 80° C. for 17 h
  2. temperatureUpon cooling to rt the reaction mixture
  3. customThe solution was transferred to a separatory funnel
  4. customthe organic layer was isolated while the aqueous layers
  5. extractionwere back extracted with EtOAc (2×25 mL)
  6. customThe combined organic layers were collected
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customto afford a brown solid

Sources & evidence

ORD record
ord-f13fe169380c41c2b83b355e50bebb05
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

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