Pyridine → HCID 66855469, compound

HRID 1970458Notes

Reaction equation

HRID 1970458 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:53])[C@@H:20]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33]([N:35]3[CH2:39][CH2:38][CH2:37][C@H:36]3[C:40](=[O:46])[NH:41][CH:42]3[CH2:45][CH2:44][CH2:43]3)=[O:34])[N:28]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[N:27]=2)=[O:25])[CH2:21][NH2:22])[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:53])[C@@H:20]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33]([N:35]3[CH2:39][CH2:38][CH2:37][C@H:36]3[C:40](=[O:46])[NH:41][CH:42]3[CH2:45][CH2:44][CH2:43]3)=[O:34])[N:28]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[N:27]=2)=[O:25])[CH2:21][NH:22][C:3](=[O:4])[CH3:2])[CH2:15][CH2:14]1)=[O:12])[CH3:9]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 66854502HCID 66854502, compound

Product 1

HCID 66855469HCID 66855469, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 100 mg 4-[(S)-3-amino-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-propionyl]-piperazine-1-carboxylic acid ethyl ester trifluoroacetate in 2 ml dichloromethane were added 32 μl pyridine, 1.6 mg DMAP and 16 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: 35 mg MS (ES+): m/e=681.

Workup

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

Sources & evidence

ORD record
ord-b8934031212747cbad635ce9b8f42d3f
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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