Diisopropylethylamine → HCID 86676679, compound

HRID 2202153Notes

Reaction equation

HRID 2202153 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:41][C:42]1[CH:50]=[CH:49][C:45]([C:46]([NH2:48])=[S:47])=[CH:44][CH:43]=1.CCN(C(C)C)C(C)C>ClCCl>[F:41][C:42]1[CH:50]=[CH:49][C:45]([C:46]([NH:48][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])=[S:47])=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 7372234-FluorothiobenzamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86676679HCID 86676679, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butoxycarbonylpiperidine-4-carboxylic acid (0.70 g, 3.05 mmol, Aldrich) and HATU (1.74 g, 4.58 mmol) were suspended in dichloromethane (10.0 ml) at room temperature for 20 minutes, followed by addition of 4-fluorothiobenzamide (0.47 g, 3.05 mmol) in one portion. The mixture was stirred at room temperature for 40 minutes, and DIEA (1.18 g, 9.16 mmol) was added. After stirring at room temperature overnight, the solvent was removed under reduced pressure. The residue was passed through a silica gel cartridge using a gradient of 0˜50% ethyl acetate in hexanes to give the title compound as a bright yellow solid.

Workup

  1. stirringAfter stirring at room temperature overnight
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ab39142419314356adbec93c30749d9e
Source dataset
uspto-grants-2016_06
Patent number
US09365539B2

Reaction notes

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