Dimethylformamide → HCID 86643697, compound

HRID 1672778Notes

Reaction equation

HRID 1672778 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=3)[C:21]([NH:23][NH2:24])=[O:22])[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:28]=1)[CH3:2].[C:29]1(CC(Cl)=O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N([CH2:44][CH3:45])CC)C.CN(C=[O:50])C>>[C:29]1([NH:24][N:23]([C:44](=[O:50])[CH3:45])[C:21](=[O:22])[C:20]2[CH:25]=[CH:26][CH:27]=[C:18]([N:15]3[CH2:14][C@H:13]4[N:9]([CH2:10][CH2:11][CH2:12]4)[C:8]4[N:28]=[C:4]([NH:3][CH2:1][CH3:2])[N:5]=[CH:6][C:7]=4[C:16]3=[O:17])[CH:19]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 67348885HCID 67348885, compound

Product 1

HCID 86643697HCID 86643697, compoundYield 66%

Procedure

(S)-3-(9-Ethylamino-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic hydrazide (220 mg, 0.576 mmol) obtained in Step 1 was dissolved in DMF (2.3 mL), and the mixture was stirred overnight at room temperature after adding phenylacetyl chloride (0.115 mL, 0.867 mmol) and triethylamine (0.161 mL, 1.15 mmol). After concentrating the mixture, the resulting residue was purified by silica gel column chromatography to give (S)-3-(9-ethylamino-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzoic acid-N′-phenyl-acetyl hydrazide (191 mg, 66%).

Workup

  1. concentrationAfter concentrating the mixture
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cfbf41dd33aa4e2782e42dbd7f44f687
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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