Sodium Iodide → HCID 25207206, compound

HRID 1255853Notes

Reaction equation

HRID 1255853 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:18]=[C:19]([C:22]([NH:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[O:23])[S:20][CH:21]=3)[CH:13]=2)[CH:5]=[CH:4][NH:3]1.Cl.Cl[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-]>>[O:1]=[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:18]=[C:19]([C:22]([NH:24][CH2:25][C:26]([F:28])([F:27])[F:29])=[O:23])[S:20][CH:21]=3)[CH:13]=2)[CH:5]=[CH:4][N:3]1[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 59603969HCID 59603969, compound

Product 1

HCID 25207206HCID 25207206, compound

Conditions

Temperature
67.5 °C

Procedure

A mixture of 4-[6-(2-oxo-1,2-dihydropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide (0.140 g, 0.334 mmol), 1-(2-chloroethyl)piperidine hydrochloride (0.092 g, 0.5 mmol), Cs2CO3 (0.435 g, 1.34 mmol), and NaI (0.010 g, 0.067 mmol) was evacuated and flushed with argon. DMF (15 mL) was added. The mixture was stirred for 16 h at 65-70° C. and evaporated. The residue was washed on a filter with water, ether, and purified on HPLC. Yield of 4-{6-[2-oxo-1-(2-piperidin-1-ylethyl)-1,2-dihydropyridin-4-yl]pyrazolo[1,5-a]pyrimidin-3-yl}-N-(2,2,2-trifluoro ethyl)thiophene-2-carboxamide (bis-TFA salt): 0.022 g. 1H NMR (400 MHz, DMSO-d6): 1.57-1.77 (4H, m), 1.82-1.92 (2H, m), 2.90-3.02 (2H, m), 3.40-3.50 m), 4.05-4.15 (2H, m), 4.33 (2H, dd, J=6.85 Hz, J=6.85 Hz), 6.98 (1H, dd, J=7.1 Hz, J=2.2 Hz), 7.13 (1H, d, J=2.2 Hz), 7.89 (1H, d, J=7.1 Hz), 8.25 (1H, d, J=1.2 Hz), 8.50 (1H, d, J=1.2 Hz), 8.73 (1H, s), 9.11 (1H, d, J=2.2 Hz), 9.17 (1H, br s), 9.23 (1H, dd, J=6.35 Hz, J=6.35 Hz), 9.70 (1H, J=2.2 Hz). LC-MS APCI: m/z 531.1 [M+H]+.

Workup

  1. customwas evacuated
  2. customflushed with argon
  3. additionDMF (15 mL) was added
  4. customevaporated
  5. washThe residue was washed on
  6. filtrationa filter with water, ether
  7. custompurified on HPLC

Sources & evidence

ORD record
ord-7fe48460bf034f688ad230a814274453
Source dataset
uspto-grants-2013_06
Patent number
US08461162B2

Reaction notes

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