Diisopropylethylamine → HCID 86685830, compound

HRID 1045801Notes

Reaction equation

HRID 1045801 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.[CH:41]([NH2:43])=[S:42].C(N(C(C)C)CC)(C)C>ClCCl>[CH:41]([NH:43][C:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)=[O:16])=[S:42]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 3005587MethanethioamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86685830HCID 86685830, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (747 mg, 3.26 mmol), HATU (1549 mg, 4.07 mmol) and the product from step A (166 mg, 2.72 mmol) were mixed in anhydrous dichloromethane (5 mL). The reaction mixture was stirred at room temperature for 30 min. N,N-diisopropyl-N-ethylamine (1.423 mL, 8.15 mmol) was added. The reaction mixture was stirred at room temperature for 16 h. The solution was concentrated and the crude was purified on SiO2 (10 to 60% ethyl acetate/hexanes) to afford the title compound. HPLC/MS: 170.1 (M−102), Rt=2.91 (LC4).

Workup

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

Sources & evidence

ORD record
ord-13dd67f2005849d6891b9ce675cd52a9
Source dataset
uspto-grants-2013_10
Patent number
US08569299B2

Reaction notes

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