Diisopropylethylamine → HCID 178492472, compound

HRID 1406379Notes

Reaction equation

HRID 1406379 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[OH:32][C:33]1[N:38]=[C:37]([C:39]([OH:41])=O)[CH:36]=[CH:35][CH:34]=1.FC(F)(F)C(O)=O.[CH3:49][O:50][C:51]1[CH:71]=[CH:70][C:54]([O:55][C:56]2[CH:69]=[CH:68][C:59]([CH2:60][NH:61][C:62]([C:64]3([NH2:67])[CH2:66][CH2:65]3)=[O:63])=[CH:58][CH:57]=2)=[C:53]([C:72]([F:75])([F:74])[F:73])[CH:52]=1>CN(C=O)C>[CH3:49][O:50][C:51]1[CH:71]=[CH:70][C:54]([O:55][C:56]2[CH:69]=[CH:68][C:59]([CH2:60][NH:61][C:62]([C:64]3([NH:67][C:39]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]([OH:32])[N:38]=4)=[O:41])[CH2:65][CH2:66]3)=[O:63])=[CH:58][CH:57]=2)=[C:53]([C:72]([F:73])([F:74])[F:75])[CH:52]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86658822HCID 86658822, compoundHCID 178524392HCID 178524392, compound

Product 1

HCID 178492472HCID 178492472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

74 μL (0.43 mmol) of DIPEA and 57.7 mg (0.18 mmol) of TBTU were added to a solution of 20 mg (0.14 mmol) of 6-hydroxypicolinic acid in 100 μL DMF and the mixture was stirred for 5 min at RT. Then 71 mg (0.14 mmol) of 1-amino-cyclopropanecarboxylic acid 4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylamide-trifluoroacetic acid salt (from 84a) was added and the mixture was stirred for 3 days at ambient temperature. The reaction mixture was purified by chromatography (reversed phase).

Workup

  1. stirringthe mixture was stirred for 3 days at ambient temperature
  2. customThe reaction mixture was purified by chromatography (reversed phase)

Sources & evidence

ORD record
ord-b55c84f94f554392a6c03e29dd7033b8
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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