6-Methylpyridine-2-carboxylic acid → HCID 58487822, compound

HRID 1406382Notes

Reaction equation

HRID 1406382 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[N:31]=[C:30]([C:32]([OH:34])=O)[CH:29]=[CH:28][CH:27]=1.FC(F)(F)C(O)=O.[CH3:42][O:43][C:44]1[CH:64]=[CH:63][C:47]([O:48][C:49]2[CH:62]=[CH:61][C:52]([CH2:53][NH:54][C:55]([C:57]3([NH2:60])[CH2:59][CH2:58]3)=[O:56])=[CH:51][CH:50]=2)=[C:46]([C:65]([F:68])([F:67])[F:66])[CH:45]=1>CN(C=O)C>[CH3:42][O:43][C:44]1[CH:64]=[CH:63][C:47]([O:48][C:49]2[CH:62]=[CH:61][C:52]([CH2:53][NH:54][C:55]([C:57]3([NH:60][C:32]([C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:25])[N:31]=4)=[O:34])[CH2:58][CH2:59]3)=[O:56])=[CH:51][CH:50]=2)=[C:46]([C:65]([F:66])([F:67])[F:68])[CH:45]=1

Participants

5

Reactant 3

HCID 702826-Methylpyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86658822HCID 86658822, compound

Product 1

HCID 58487822HCID 58487822, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28 μL (0.20 mmol) of TEA and 118.8 mg (0.30 mmol) of HATU were added to a solution of 27.7 mg (0.20 mmol) of 6-methylpicolinic acid in 5 mL DMF and the mixture was stirred for 5 min at RT. Then 112 μL (0.81 mmol) of TEA and 100 mg (0.20 mmol) of 1-amino-cyclopropanecarboxylic acid 4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylamide-trifluoroacetic acid salt (from 85a) were added and the mixture was stirred overnight at RT. The reaction mixture was purified by chromatography (reversed phase).

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. customThe reaction mixture was purified by chromatography (reversed phase)

Sources & evidence

ORD record
ord-7a8e5248a008438d8a7ca659ecc63052
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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