Triethylamine → N-{4-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]butyl}isoxazole-3-carboxamide

HRID 629928Notes

Reaction equation

HRID 629928 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][CH2:43][CH2:44][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>ClCCl>[CH3:56][C:55]([CH3:58])([CH3:57])[CH2:54][N:53]1[C:48]2[C:49](=[N:50][C:45]([CH2:44][CH2:43][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 711367765-(4-Aminobutyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 71136780N-{4-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]butyl}isoxazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-isoxazolecarboxylic acid (0.02 g, 0.18 mmol), and triethylamine (0.1 mL, 0.72 mmol) in dichloromethane (2 mL) was added HATU (0.07 g, 0.18 mmol). The resulting mixture was stirred 20 minutes. To this mixture was added 38-2 (0.04 g, 0.14 mmol) and the resulting mixture was stirred room temperature overnight. The mixture was washed with water and concentrated. Flash column separation using a 10-70% ethyl acetate/hexane gradient gave 38-3. (0.045 g, 85%). HRMS (M+H)+: observed=386.2188, 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 38-3

Sources & evidence

ORD record
ord-6c54fdecc69c4d66908976e7e64a0fec
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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