Picolinic acid → tert-butyl-N-(1-{[4-chloro-6-(pyridine-2-amido)pyridin-2-yl]carbamoyl}-ethyl)carbamate

HRID 1772168Notes

Reaction equation

HRID 1772168 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30](=[O:45])[NH:31][CH:32]([C:34](=[O:44])[NH:35][C:36]1[CH:41]=[C:40]([Cl:42])[CH:39]=[C:38]([NH2:43])[N:37]=1)[CH3:33])([CH3:28])([CH3:27])[CH3:26].[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52](O)=[O:53].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[C:25]([O:29][C:30](=[O:45])[NH:31][CH:32]([C:34](=[O:44])[NH:35][C:36]1[CH:41]=[C:40]([Cl:42])[CH:39]=[C:38]([NH:43][C:52]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][N:46]=2)=[O:53])[N:37]=1)[CH3:33])([CH3:26])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117903116tert-butyl-N-{1-[(6-amino-4-chloropyridin-2-yl)carbamoyl]ethyl}carbamate

Product 1

HCID 117902536tert-butyl-N-(1-{[4-chloro-6-(pyridine-2-amido)pyridin-2-yl]carbamoyl}-ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

HATU (180 mg, 0.47 mmol) is added to a mixture of tert-butyl-N-{1-[(6-amino-4-chloropyridin-2-yl)carbamoyl]ethyl}carbamate J8 (100 mg, 0.32 mmol), pyridine-2-carboxylic acid (60 mg, 0.49 mmol) and DIPEA in NMP (1.5 ml) and the mixture is stirred at RT for 2 h and stirring continued at 50° C. for 17 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 27 mg (20%). HPLC-MS: M+H=420 (Method—2).

Workup

  1. stirringstirring
  2. waitcontinued at 50° C. for 17 h
  3. concentrationThe mixture is concentrated in vacuo
  4. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-492960fd365140eb8d70ee9c53b40b71
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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