Diisopropylethylamine → HCID 10425517, compound

HRID 1768369Notes

Reaction equation

HRID 1768369 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(#N)C>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:15]1[CH2:16][CH2:17][N:12]([CH2:2][C:3]2[S:4][C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[CH:7][N:6]=3)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 103747502-(Piperidin-4-yl)pyridineHCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 10425517HCID 10425517, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product from Example 38A (50 mg, 0.11 mmol), 2-(4-piperidinyl)pyridine (25 mg, 0.13 mmol), and DIEA (340 μL, 2.1 mmol) were combined in acetonitrile (1 mL) and stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure. The residue was treated with hot methanol. The methanol was filtered and the filter cake washed with cold methanol to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.13 (m, 4H), 3.13 (m, 4H), 3.61 (m, 3H), 7.38 (d, J=4.75 Hz, 1H), 7.76(dd, J=8.3 Hz, 4.6 Hz, 1H), 7.91 (m, 1H), 8.31 (m, 1H), 8.54 (m, 2H), 8.72 (dd, J=4.6 hz, 1.53 Hz, 1H); (ESI) m/z 311 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was treated with hot methanol
  3. filtrationThe methanol was filtered
  4. washthe filter cake washed with cold methanol

Sources & evidence

ORD record
ord-0d09d5748b544ace998c9479609f59ff
Source dataset
uspto-grants-2007_06
Patent number
US07235661B2

Reaction notes

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