2-(Tributylstannyl)-1,3-thiazole → HCID 57442336, compound

HRID 2262714Notes

Reaction equation

HRID 2262714 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[O:16])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:32]1[S:33][CH:34]=[CH:35][N:36]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:23]1([N:20]2[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][N:11]3[CH2:12][CH2:13][N:8]([C:5]4[N:4]=[N:3][C:2]([C:32]5[S:33][CH:34]=[CH:35][N:36]=5)=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)[CH2:18][CH2:19]2)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 57443120HCID 57443120, compound

Product 1

HCID 57442336HCID 57442336, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a sealed tube, dissolve 3-chloro-6-{4-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-piperazin-1-yl}pyridazine (100 mg, 0.264 mmol), and 2-tributylstannylthiazole (197 mg, 0.528 mmol), Pd(PPh3)4 (30 mg, 0.262 mmol) in toluene (5 mL). Degas with N2 and seal the tube. Heat the mixture at 120° C. overnight. Cool and filter the solution through Celite. Wash the Celite bed with EtOAc (25 mL). Evaporate the solvent and dissolve the residue in 3N HCl (50 mL). Extract with CH2Cl2 (2×25 mL). Discard these organic extracts. Basify the aqueous phase with 10 N NaOH and extract with CH2Cl2 (2×40 mL). Combine these organic extracts and wash once with saturated aqueous KF solution (50 mL). Dry the organic extract and evaporate to yield the title compound. 1H NMR (CDCl3) δ 8.07 (d, 1H) 7.88 (d, 1H), 7.37 (d, 1H) 6.99 (d, 1H), 3.78 (t, 4H), 3.66-3.62 (m, 4H), 3.26 (s, 2H), 2.75-2.66 (m, 5H), 2.35-2.29 (m, 4H), 2.07-2.00 (m, 2H), 1.90-1.84 (m, 2H), 1.74-1.71 (m, 2H); LC-MS (M+1) 428.17.

Workup

  1. customDegas with N2
  2. customseal the tube
  3. temperatureCool
  4. filtrationfilter the solution through Celite
  5. washWash the Celite bed with EtOAc (25 mL)
  6. customEvaporate the solvent
  7. dissolutiondissolve the residue in 3N HCl (50 mL)
  8. extractionExtract with CH2Cl2 (2×25 mL)
  9. extractionBasify the aqueous phase with 10 N NaOH and extract with CH2Cl2 (2×40 mL)
  10. washCombine these organic extracts and wash once with saturated aqueous KF solution (50 mL)
  11. customDry the
  12. extractionorganic extract
  13. customevaporate

Sources & evidence

ORD record
ord-5c00c0894aea4ec6ac2a6c2a1c2105cd
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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