Triethylamine → HCID 25231884, compound

HRID 1406376Notes

Reaction equation

HRID 1406376 reaction equation
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:30][C:31]1[C:35]([C:36]([OH:38])=O)=[CH:34][O:33][N:32]=1.[CH3:39][O:40][C:41]1[CH:61]=[CH:60][C:44]([O:45][C:46]2[CH:59]=[CH:58][C:49]([CH2:50][NH:51][C:52]([C:54]3([NH2:57])[CH2:56][CH2:55]3)=[O:53])=[CH:48][CH:47]=2)=[C:43]([C:62]([F:65])([F:64])[F:63])[CH:42]=1>CN(C=O)C>[CH3:39][O:40][C:41]1[CH:61]=[CH:60][C:44]([O:45][C:46]2[CH:59]=[CH:58][C:49]([CH2:50][NH:51][C:52]([C:54]3([NH:57][C:36]([C:35]4[C:31]([CH3:30])=[N:32][O:33][CH:34]=4)=[O:38])[CH2:55][CH2:56]3)=[O:53])=[CH:48][CH:47]=2)=[C:43]([C:62]([F:63])([F:64])[F:65])[CH:42]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 45896923-Methyl-1,2-oxazole-4-carboxylic acidHCID 67448480HCID 67448480, compound

Product 1

HCID 25231884HCID 25231884, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

37 μL (0.26 mmol) of triethylamine and 84.4 mg (0.26 mmol) of TBTU were added to a solution of 33.4 mg (0.26 mmol) of 3-methylisoxazole-4-carboxylic acid in 5 mL DMF and the mixture was stirred for 10 min at RT. Then 100 mg (0.26 mmol) of 1-amino-cyclopropanecarboxylic acid 4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylamide (from 85a) was added and the mixture was stirred for 4 h at ambient temperature and overnight at 40° C. The reaction mixture was purified by chromatography (reversed phase).

Workup

  1. stirringthe mixture was stirred for 4 h at ambient temperature and overnight at 40° C
  2. customThe reaction mixture was purified by chromatography (reversed phase)

Sources & evidence

ORD record
ord-018ac5029cbe47ee81c19bdecaa96f90
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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