Diisopropylethylamine → HCID 178452383, compound

HRID 1970647Notes

Reaction equation

HRID 1970647 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:35])[CH2:15][NH:16][C:17]([C:19]2[CH:23]=[C:22]([O:24][CH2:25][C:26](O)=[O:27])[N:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:69]1[CH2:73][CH2:72][CH2:71][C@H:70]1[C:74]1[NH:78][N:77]=[N:76][N:75]=1>CN(C=O)C.ClCCl>[CH2:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:35])[CH2:15][NH:16][C:17]([C:19]2[CH:23]=[C:22]([O:24][CH2:25][C:26](=[O:27])[N:69]3[CH2:73][CH2:72][CH2:71][C@H:70]3[C:74]3[NH:78][N:77]=[N:76][N:75]=3)[N:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:20]=2)=[O:18])[CH2:12][CH2:13]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668555664-{2-[(5-Carboxymethoxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl esterHCID 178420796HCID 178420796, compound

Product 1

HCID 178452383HCID 178452383, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 193 mg 4-{2-[(5-Carboxymethoxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester in 2 ml DMF were added 150 mg HATU and 69 μl DIPEA. After 10 minutes a solution of 54 mg (S)-5-Pyrrolidin-2-yl-1H-tetrazole in 1 ml DMF was added and after 36 h the reaction mixture was diluted with dichloromethane and extracted with aqueous LiCl (4%), 0.1 M HCl and brine. The crude product thus obtained after evaporation of the solvent was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were immediately lyophilized to yield the title compound

Workup

  1. extractionextracted with aqueous LiCl (4%), 0.1 M HCl and brine
  2. customThe crude product thus obtained
  3. customafter evaporation of the solvent
  4. customwas purified by preparative HPLC (
  5. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  6. additionThe fractions containing the product

Sources & evidence

ORD record
ord-d86cb8aca6154e6a90589b9c588f5f05
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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