Diisopropylethylamine → HCID 86685826, compound

HRID 1045798Notes

Reaction equation

HRID 1045798 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.[C:41]([NH2:44])(=[S:43])[CH3:42].C(N(C(C)C)CC)(C)C>ClCCl>[C:41]([NH:44][C:14]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)=[O:16])(=[S:43])[CH3:42]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 2723949ThioacetamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86685826HCID 86685826, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid (2.213 g, 9.65 mmol), HATU (4.050 g, 10.65 mmol) and thioacetamide (1.597 g, 21.26 mmol) were mixed in anhydrous dichloromethane (25 mL). The reaction mixture was stirred at room temperature for 30 min. N,N-diisopropyl-N-ethylamine (5.3 mL, 30.3 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The solution was concentrated and the crude residue was purified on SiO2 (10 to 60% ethyl acetate, hexanes) to afford the title compound, which was used without further purification. HPLC/MS: 112.1 (M−174), Rt=3.00 (LC4).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 h
  2. concentrationThe solution was concentrated
  3. customthe crude residue was purified on SiO2 (10 to 60% ethyl acetate, hexanes)

Sources & evidence

ORD record
ord-629453b69f5242d98345a60799715744
Source dataset
uspto-grants-2013_10
Patent number
US08569299B2

Reaction notes

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