Ammonia → HCID 86760621, compound

HRID 2116625Notes

Reaction equation

HRID 2116625 reaction equation
[N:1]([C@@H:4]([CH3:18])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15](O)=[O:16])[CH:13]=2)[CH:8]=[N:7]1)=[N+:2]=[N-:3].C1C=CC2N(O)N=[N:25]C=2C=1.CCN=C=NCCCN(C)C.N.O1CCOCC1.[Cl-].[NH4+]>CN(C=O)C>[N:1]([C@@H:4]([CH3:18])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([NH2:25])=[O:16])[CH:13]=2)[CH:8]=[N:7]1)=[N+:2]=[N-:3]

Participants

8

Reactant 6

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 86760622HCID 86760622, compound

Product 1

HCID 86760621HCID 86760621, compoundYield 191.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the product from Step A (0.17 g, 0.64 mmol) in DMF (5 mL) was added HOBT (0.041 g, 0.30 mmol), and EDCI (0.18 g, 0.96 mmol), followed by a solution of ammonia in dioxane (0.5 M, 0.18 g, 0.96 mmol). After 18 h, a saturated aqueous solution of ammonium chloride (20 mL) was added. The mixture was extracted with ethyl acetate (3×50 mL) and the combined extracts were washed with brine, dried and evaporated. The residue was purified by chromatography (silica, 50% ethyl acetate in hexane, ethyl acetate) to give an oil (0.14 g, 92%): MS (ES) m/z 245 (M+); 1H NMR (CDCl3) 8.11 (1H, s), 8.08 (1H, s), 7.81 (1H, d, J=8.0 Hz), 7.52 (1H, d, J=8.0 Hz), 4.43 (2H, m), 4.15 (1H, m), 1.36 (3H, d, J=8.0 Hz).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  2. washthe combined extracts were washed with brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by chromatography (silica, 50% ethyl acetate in hexane, ethyl acetate)

Sources & evidence

ORD record
ord-c772261e0138426c8193e8fdb3183497
Source dataset
uspto-grants-2008_10
Patent number
US07439262B1

Reaction notes

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