O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 58487763, compound

HRID 1406381Notes

Reaction equation

HRID 1406381 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[O:23]1[C:27]([C:28]([OH:30])=O)=[CH:26][N:25]=[CH:24]1.FC(F)(F)C(O)=O.[CH3:38][O:39][C:40]1[CH:60]=[CH:59][C:43]([O:44][C:45]2[CH:58]=[CH:57][C:48]([CH2:49][NH:50][C:51]([C:53]3([NH2:56])[CH2:55][CH2:54]3)=[O:52])=[CH:47][CH:46]=2)=[C:42]([C:61]([F:64])([F:63])[F:62])[CH:41]=1>CN(C=O)C>[CH3:38][O:39][C:40]1[CH:60]=[CH:59][C:43]([O:44][C:45]2[CH:58]=[CH:57][C:48]([CH2:49][NH:50][C:51]([C:53]3([NH:56][C:28]([C:27]4[O:23][CH:24]=[N:25][CH:26]=4)=[O:30])[CH2:54][CH2:55]3)=[O:52])=[CH:47][CH:46]=2)=[C:42]([C:61]([F:62])([F:63])[F:64])[CH:41]=1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 16340557Oxazole-5-carboxylic AcidHCID 86658822HCID 86658822, compound

Product 1

HCID 58487763HCID 58487763, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

57.5 μL (0.41 mmol) of TEA and 48 mg (0.15 mmol) of TBTU were added to a solution of 15.4 mg (0.14 mmol) of oxazole-5-carboxylic acid in 1.5 mL DMF and the mixture was stirred for 5 min at RT. Then 67.5 mg (0.14 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 for 2 h at ambient temperature. The reaction mixture was purified by chromatography (reversed phase).

Workup

  1. stirringthe mixture was stirred for 2 h at ambient temperature
  2. customThe reaction mixture was purified by chromatography (reversed phase)

Sources & evidence

ORD record
ord-8c8557dee92c4c11928b839a02813114
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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