Diisopropylethylamine → HCID 70896520, compound

HRID 1619290Notes

Reaction equation

HRID 1619290 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[CH3:22][NH:23][C:24]([CH3:27])([CH3:26])[CH3:25].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[C:24]([N:23]([CH3:22])[C:8]([C:5]1[C:4]([C:11]#[N:12])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:10])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 84552N-Methyl-tert-butylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70896531HCID 70896531, compound

Product 1

HCID 70896520HCID 70896520, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-bromo-3-cyano-pyridine-2-carboxylic acid (100 mg, 0.44 mmol) in dichloromethane (5 ml) at 0° C. were added DIPEA (0.226 ml, 1.32 mmol, 3 equiv.), methyl tert-butyl amine (0.079 ml, 0.661 mmol, 1.5 equiv.) and HBTU (250 mg, 0.661 mmol, 1.5 equiv.). The reaction mixture was stirred at 25° C. for 14 hours. The solvent was removed in vacuum and the resulting crude material was purified by column chromatography over normal silica gel (10-20% EtOAc in hexane) to afford 5-bromo-3-cyano-pyridine-2-carboxylic acid tert-butyl-methyl-amide (85 mg, 65%) as colorless oil.

Workup

  1. customThe solvent was removed in vacuum
  2. customthe resulting crude material was purified by column chromatography over normal silica gel (10-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-ce7f018c4a6f44259cf83bcc62787a34
Source dataset
uspto-grants-2014_07
Patent number
US08772300B2

Reaction notes

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