Pyridine → HCID 44128900, compound

HRID 1970460Notes

Reaction equation

HRID 1970460 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[CH2:8]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:54])[C@@H:20]([NH:24][C:25]([C:27]2[CH:31]=[C:30]([O:32][CH2:33][C:34]([N:36]3[CH2:40][CH2:39][CH2:38][C@H:37]3[C:41](=[O:47])[NH:42][CH:43]3[CH2:46][CH2:45][CH2:44]3)=[O:35])[N:29]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:28]=2)=[O:26])[CH2:21][CH2:22][NH2:23])[CH2:15][CH2:14]1)=[O:12])[CH3:9].N1C=CC=CC=1.CC(OC(C)=O)=O>ClCCl.CN(C1C=CN=CC=1)C>[CH2:8]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:54])[C@@H:20]([NH:24][C:25]([C:27]2[CH:31]=[C:30]([O:32][CH2:33][C:34]([N:36]3[CH2:40][CH2:39][CH2:38][C@H:37]3[C:41](=[O:47])[NH:42][CH:43]3[CH2:46][CH2:45][CH2:44]3)=[O:35])[N:29]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:28]=2)=[O:26])[CH2:21][CH2:22][NH:23][C:3](=[O:4])[CH3:2])[CH2:15][CH2:14]1)=[O:12])[CH3:9]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 668549184-[(S)-4-amino-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester trifluoroacetate

Product 1

HCID 44128900HCID 44128900, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 302 mg 4-[(S)-4-amino-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester trifluoroacetate in 5 ml dichloromethane were added 96 μl pyridine, 5 mg DMAP and 48 μl Ac2O at 0° C. After 1 h stirring at this temperature the reaction mixture was diluted with dichloromethane and washed with 0.1 M HCl and half-saturated aqueous NaHCO3. The crude product 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). Yield: 27 mg MS (ES+): m/e=695.

Workup

  1. washwashed with 0.1 M HCl and half-saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-7fe58454fe174680a06bbb2a70caea97
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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