2-Pyridineethanamine → HCID 22046412, compound

HRID 1821752Notes

Reaction equation

HRID 1821752 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:16][C:17]([NH:19][C:20]2[CH:25]=[N:24][C:23]([CH3:26])=[CH:22][N:21]=2)=[O:18])=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:51][CH2:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[C:4]([NH:16][C:17]([NH:19][C:20]2[CH:25]=[N:24][C:23]([CH3:26])=[CH:22][N:21]=2)=[O:18])=[CH:5][C:6]([C:12]([F:15])([F:13])[F:14])=[C:7]([CH:11]=1)[C:8]([NH:51][CH2:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=1)=[O:9]

Participants

6

Reactant 4

HCID 759192-PyridineethanamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22046499HCID 22046499, compound

Product 1

HCID 22046412HCID 22046412, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 5-methoxy-4-[3-(5-methyl-pyrazin-2yl)-ureido]-2-trifluoromethyl-benzoic acid (37 mg, 0.1 mmol) in 1 mL NMP at room temperature in a capped reaction vial was added HBTU (42 mg, 0.11 mmol) and the suspension stirred for 15 minutes. 2-aminoethylpyridine (13 μL, 0.11 mmol) was added followed by DIEA (35 μL, 0.2 mmol) and the reaction was stirred overnight. NMP was then removed by bulb to bulb transfer under high vacuum at 70° C. and the residue triturated and filtered with EtOAc to give the desired amide as a tan solid (32 mg, 68%).

Workup

  1. stirringthe reaction was stirred overnight
  2. customNMP was then removed by bulb to bulb transfer under high vacuum at 70° C.
  3. customthe residue triturated
  4. filtrationfiltered with EtOAc

Sources & evidence

ORD record
ord-ebe29d17ee9f4a0d880b802f095be413
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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