p-Toluenesulfonic acid → HCID 24986498, compound

HRID 388542Notes

Reaction equation

HRID 388542 reaction equation
[CH2:1]([N:8]1[CH2:42][CH2:41][C:11]2([N:15]([C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[C:14](=[O:33])[N:13]=[C:12]2[NH:34][CH2:35][CH:36](OC)OC)[CH2:10][CH:9]1[CH3:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:42][CH2:41][C:11]2([C:12]3=[N:34][CH:35]=[CH:36][N:13]3[C:14](=[O:33])[N:15]2[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:25][CH:24]=2)[CH2:10][CH:9]1[CH3:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178495894HCID 178495894, compound

Product 1

HCID 24986498HCID 24986498, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 8-benzyl-4-[(2,2-dimethoxyethyl)amino]-1-[4-fluoro-4′-(methylsulfonyl)biphenyl-2-yl]-7-methyl-1,3,8-triazaspiro[4.5]dec-3-en-2-one (50 mg, 0.08 mmol) in toluene (2.0 ml) was added p-toluenesulfonic acid (20 mg, 0.01 mmol). The reaction was sealed and allowed to stir at 110° C. The reaction was purified via reverse phase chromatography and neutralized with sodium bicarbonate. The product was extracted with EtOAc, dried over sodium sulfate, filtered, and concentrated in vacuo to yield the title compound as cis and trans mixture-1′-benzyl-6-[4-fluoro-4′-(methylsulfonyl)biphenyl-2-yl]-2′-methylspiro[imidazo[1,5-a]imidazole-7,4′-piperidin]-5(6H)-one. LCMS (M+H) 544.9. 1H NMR (400 MHz, CD3OD) δ 7.98 (m, 1H), 7.89 (m, 1H), 7.66 (m, 3H), 7.55 (m, 1H), 7.46 (m, 1H), 7.40 (dt, J=8.8, 2.8 Hz, 0.5H), 7.32 (dt, J=9.2, 2.8 Hz, 0.5H), 7.22 (m, 5H), 6.91 (m, 0.5H), 6.79 (m, 0.5H), 4.10 (m, 1H), 3.12 (s, 1.5H), 3.06 (s, 1.5H), 3.02 (s, 1H), 2.81 (m, 1H), 2.71-2.40 (m, 2H), 2.04-1.85 (m, 1H), 1.78-1.57 (m, 3H), 1.32 (s, 3H).

Workup

  1. customThe reaction was sealed
  2. customThe reaction was purified via reverse phase chromatography
  3. extractionThe product was extracted with EtOAc
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8d84d5acc40487bacd8af61f27898dc
Source dataset
uspto-grants-2013_02
Patent number
US08377954B2

Reaction notes

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