Triethylamine → HCID 44476316, compound

HRID 2192514Notes

Reaction equation

HRID 2192514 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[O:42][CH:43]([CH3:45])[CH3:44])[C:36]([OH:38])=O.O[NH:47][C:48]([C:50]1[C:51]2[CH:52]=[CH:53][N:54]=[CH:55][C:56]=2[CH:57]=[CH:58][CH:59]=1)=[NH:49]>>[Cl:32][C:33]1[CH:34]=[C:35]([C:36]2[O:38][N:49]=[C:48]([C:50]3[CH:59]=[CH:58][CH:57]=[C:56]4[C:51]=3[CH:52]=[CH:53][N:54]=[CH:55]4)[N:47]=2)[CH:39]=[CH:40][C:41]=1[O:42][CH:43]([CH3:45])[CH3:44]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178513273HCID 178513273, compound

Product 1

HCID 44476316HCID 44476316, compoundYield 37.8%

Procedure

A microwave vial was charged with HATU (2.5 g, 6.57 mmol), triethylamine (1.48 ml, 10.7 mmol), 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D3; 1.15 g, 5.34 mmol) and N-hydroxy-5-isoquinolinecarboximidamide (D1; 1 g, 5.34 mmol). The solution was stirred at room temperature for 30 minutes. The reaction vessel was sealed and heated under microwave irradiation at 130° C. for 120 min. After cooling, the reaction mixture was filtered. The isolated grey-brown solid was washed with acetonitrile before being dried in vacuo at 60° C. to give the title compound as a grey solid (738 mg, 37%).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated under microwave irradiation at 130° C. for 120 min
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. washThe isolated grey-brown solid was washed with acetonitrile
  6. custombefore being dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-70fa40092edf4600afcd5c8de4f6e18a
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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