Toluene → HCID 117926390, compound

HRID 1054204Notes

Reaction equation

HRID 1054204 reaction equation
[CH2:1]([N:8]1[C:13](=O)[C:12]2[CH:15]=[CH:16][CH:17]=[N:18][C:11]=2[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:34]2)=CC=1.C1(C)C=CC=CC=1>[Cl-].[Na+].O>[CH2:1]([N:8]1[C:13](=[S:34])[C:12]2[CH:15]=[CH:16][CH:17]=[N:18][C:11]=2[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagent3×HCID 117926313HCID 117926313, compound

Product 1

HCID 117926390HCID 117926390, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 6-benzyl-8-(pyridin-2-yl)pyrido[2,3-d]pyridazin-5(6H)-one RL-10 (45 mg, 0.143 mmol), 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (57 mg, 0.143 mmol), and 4 mL of toluene were heated to 115° C. for 2 h. Another 35 mg aliquot of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide was added and the heating was continued for 2 h. Still another 35 mg aliquot of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide was added and heating continued for an additional 2 h. After cooling, the reaction mixture was poured into 15 mL of saturated brine and then extracted with 4×20 mL of ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and dried overnight at 60° C. under vacuum to give 6-benzyl-8-(pyridine-2-yl)pyrido[2,3-d]pyridazine-5(6H)-thione RL-11 (31 mg, 0.94 mmol). 1H NMR (400 MHz, Chloroform-d) δ 9.25 (dd, J=8.4, 1.7 Hz, 1H), 9.19-9.12 (m, 1H), 9.03 (s, 1H), 8.13 (bd, J=57.3 Hz, 1H), 7.72 (dd, J=8.4, 4.4 Hz, 1H), 7.64-7.52 (m, 3H), 7.40-7.25 (m, 4H), 6.17 (s, 2H). LCMS: (M+H)+, 331.

Workup

  1. temperatureheating
  2. waitcontinued for an additional 2 h
  3. temperatureAfter cooling
  4. extractionextracted with 4×20 mL of ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customdried overnight at 60° C. under vacuum

Sources & evidence

ORD record
ord-a1d027abadf4424aa1255eb6b384f187
Source dataset
uspto-grants-2016_07
Patent number
US09394299B2

Reaction notes

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