Triethylamine → HCID 117702393, compound

HRID 629922Notes

Reaction equation

HRID 629922 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[N:2]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:40][CH2:41][CH2:42][C@@H:43]([C:45]1[N:50]=[C:49]2[N:51]([CH3:60])[C:52](=[O:59])[N:53]([CH2:54][C:55]([CH3:58])([CH3:57])[CH3:56])[C:48]2=[CH:47][CH:46]=1)[CH3:44]>ClCCl>[CH3:57][C:55]([CH3:56])([CH3:58])[CH2:54][N:53]1[C:48]2[C:49](=[N:50][C:45]([C@H:43]([CH3:44])[CH2:42][CH2:41][NH:40][C:6]([C:3]3[CH:4]=[CH:5][O:1][N:2]=3)=[O:8])=[CH:46][CH:47]=2)[N:51]([CH3:60])[C:52]1=[O:59]

Participants

6

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 112864533-Isoxazolecarboxylic acidHCID 71136767HCID 71136767, compound

Product 1

HCID 117702393HCID 117702393, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-Isoxazolecarboxylic acid (0.015 g, 0.13 mmol), and triethylamine (0.1 mL, 0.72 mmol) in dichloromethane (2 mL) was added HATU (0.05 g, 0.13 mmol). The resulting mixture was stirred 20 minutes. To this mixture was added 36-4 (0.03 g, 0.10 mmol) and the resulting mixture was stirred room temperature overnight. The mixture was washed with water and concentrated. Flash column separation using a 0-60% ethyl acetate/hexane gradient, followed by 10-90% reverse phase gradient gave 36-5. (0.017 g, 43%). HRMS (M+H)+: observed=386.2189, calculated=386.2187

Workup

  1. stirringthe resulting mixture was stirred room temperature overnight
  2. washThe mixture was washed with water
  3. concentrationconcentrated
  4. customFlash column separation
  5. customgave 36-5

Sources & evidence

ORD record
ord-a9fdaa5269834a6aaaea13773d20a351
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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