Triethylamine → HCID 67215741, compound

HRID 1677578Notes

Reaction equation

HRID 1677578 reaction equation
C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=1)[C:40](O)=[O:41].[NH2:46][C:47]1[N:48]=[C:49]([C:56]([C:58]2[CH:63]=[CH:62][C:61]([N+:64]([O-:66])=[O:65])=[C:60]([O:67][CH3:68])[CH:59]=2)=[O:57])[N:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=12>C(#N)C.O.C(OCC)(=O)C>[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=1)[C:40]([NH:46][C:47]1[N:48]=[C:49]([C:56](=[O:57])[C:58]2[CH:63]=[CH:62][C:61]([N+:64]([O-:66])=[O:65])=[C:60]([O:67][CH3:68])[CH:59]=2)[N:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=12)=[O:41]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 114613-Methoxybenzoic AcidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67215846(1-Aminoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone

Product 1

HCID 67215741HCID 67215741, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.78 ml (5.05 mmol) of triethylamine and then 1.17 g (2.65 mmol) of BOP are added, under a nitrogen atmosphere, to 0.8 g (2.29 mmol) of 3-methoxybenzoic acid in 20 ml of acetonitrile. After stirring at ambient temperature for 30 minutes, 0.8 g (2.29 mmol) of (1-aminoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone obtained in example 76 is added and then the mixture is heated at 80° C. for 20 hours. The reaction medium is taken up in a mixture of water and ethyl acetate. The organic phase is separated by settling, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel, elution being carried out with a dichloromethane/acetone (99/1) mixture. 0.618 g of an orange-colored solid is collected. Melting point: 167° C.; 1H NMR (d6-DMSO): 3.87 (3H, s), 4.02 (3H, s), 7.21 (1H, d), 7.41-7.49 (3H, m), 7.63-7.66 (2H, m), 7.95-8.10 (3H, m), 8.11 (1H, s), 9.80 (1H, d)

Workup

  1. temperaturethe mixture is heated at 80° C. for 20 hours
  2. customThe organic phase is separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel, elution
  7. custom0.618 g of an orange-colored solid is collected

Sources & evidence

ORD record
ord-f0620891115442b8baf14d3e65001603
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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