Diisopropylethylamine → HCID 49763920, compound

HRID 1182670Notes

Reaction equation

HRID 1182670 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:46]([O:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:60])[CH2:58][NH2:59])[CH2:53][CH2:52]1)=[O:50])[CH3:47]>CN(C=O)C>[CH2:46]([O:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:60])[CH2:58][NH:59][C:12]([C:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8][CH:9]=2)=[O:14])[CH2:53][CH2:52]1)=[O:50])[CH3:47]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1389282-Phenyl-4-carboxythiazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22017388HCID 22017388, compound

Product 1

HCID 49763920HCID 49763920, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 2-phenyl-1,3-thiazole-4-carboxylic acid (5.1 mg) and DIPEA (3 eq) in DMF (0.4 mL) was added TBTU (1.2 eq) in DMF (0.2 mL). Then, a solution of 4-(2-amino-acetyl)-piperazine-1-carboxylic acid ethyl ester (5.4 mg, prepared as described in WO2006114774) in DMF (0.2 mL) was added. After stirring overnight at RT, the reaction mixture was directly purified by preparative HPLC (IV) to give 4.9 mg of the desired product.

Workup

  1. customthe reaction mixture was directly purified by preparative HPLC (IV)

Sources & evidence

ORD record
ord-562e7c56b4b346a3940ce6373b743d87
Source dataset
uspto-grants-2014_03
Patent number
US08664203B2

Reaction notes

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