Ammonia → HCID 67198596, compound

HRID 547553Notes

Reaction equation

HRID 547553 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24].N>O1CCOCC1.O>[NH2:16][C:11]1[N:10]=[C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:1][C:30](=[O:31])[C:29]3[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:34][CH:33]=3)[CH:7]=[CH:6][CH:5]=2)[CH:14]=[C:13]([CH3:15])[N:12]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 86621644HCID 86621644, compound

Product 1

HCID 67198596HCID 67198596, compoundYield 103.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of diamine E2 (5.25 g, 20.85 mmol) and dry pyridine (8.40 mL, 104.26 mmol) in dry dioxane (200 mL) was added 4-nitrobenzoyl chloride (10.79 g, 58.13 mmol), and the resulting solution was refluxed for ˜14 h. After this time, the reaction mixture was cooled to room temperature, and then basified by addition of aqueous ammonia solution. The resulting solution was diluted with H2O, and the resulting precipitate collected by filtration to afford amide E3 as an amorphous yellow-brown solid (7.89 g, 94%) [a small sample of this crude material was reprecipitated from acidified MeOH:EtOAc for characterisation, whilst the bulk was used without further purification]; 1H NMR (400 MHz, DMSO): δ 12.99 (br s, 1H, pyrimidinyl-N+—H), 10.82 (s, 1H, ArNHAr), 10.76 (br s, 1H, ArC(O)NHAr), 8.35 (dd, J=6.92, 1.99 Hz, 2H, ArH), 8.27 (d, J=6.92, 1.99 Hz, 2H, ArH), 7.90 (v v v br s, 2H, ArNH2), 8.20-7.50 (m, 4H, ArH & ArNH2), 7.45-7.10 (m, 2H, ArH), 6.25 (s, 1H, ArH), 2.28 (s, 3H, ArCH3); LCMS (APCI+): 365 (100%).

Workup

  1. temperaturethe resulting solution was refluxed for ˜14 h
  2. filtrationthe resulting precipitate collected by filtration

Sources & evidence

ORD record
ord-4a26c1994b2e4558b790ee5c82d08743
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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