2-Thiocresol → HCID 89395585, compound

HRID 713419Notes

Reaction equation

HRID 713419 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].CCN([CH:23]([CH3:25])[CH3:24])C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:50][C:51]1C=CC=[CH:53][C:52]=1[SH:57]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([S:57][C:52]2[CH:53]=[CH:25][C:23]([CH3:24])=[CH:50][CH:51]=2)=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 87122-ThiocresolHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 89395585HCID 89395585, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (5 g, 21.8 mmol, 1 eq.) and DIEA (7.6 mL, 44 mmol, 2 eq.) in DMF was added HATU (9.12 g, 24 mmol, 1.1 eq.) and stirred at room temperature for 30 min. Methylbenzenethiol (3 g, 24 mmol, 1.1 eq.) in 45 mL of DMF was added and the resulting mixture was stirred at room temperature overnight. After 18 h, the reaction mixture was concentrated in vacuo to give an oil. This oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptane) to give the title compound as a white solid (6.6 g, 90% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.28 (m, 4H), 4.13 (m, 2H), 2.81 (m, 3H), 2.39 (s, 3H), 1.97 (m, 2H), 1.73 (m, 2H), 1.48 (s, 9H), MS (ESI) m/z 336.6 (M+H)+. Exact mass calculated for C18H26N1O3S, 336.2. MS (ESI) m/z 279.9 (M+H without t-butyl). Retention time: 1.27 min (5-95% CH3CN/H2O over 2 min with 0.1% formic acid, Inertsil 3×3 mm C-8-3 column with flow rate of 2 mL/min).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. waitAfter 18 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customto give an oil
  5. customThis oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-1db27c91e8a4404788cb659b88d6249d
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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