Benzenesulfonyl chloride → HCID 59507102, compound

HRID 1400114Notes

Reaction equation

HRID 1400114 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]4[C:19](=[O:20])[N:18]([CH2:21][CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:17](=[O:29])[C:15]4=3)[N:10]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:46]1([S:52](Cl)(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>ClCCl>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][N:10]2[C:11]3=[N:12][CH:13]=[C:14]4[C:19](=[O:20])[N:18]([CH2:21][CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:17](=[O:29])[C:15]4=[C:16]3[C:8]([C:4]3[CH:3]=[C:2]([NH:1][S:52]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)(=[O:54])=[O:53])[CH:7]=[CH:6][CH:5]=3)=[N:9]2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 59507160HCID 59507160, compound

Product 1

HCID 59507102HCID 59507102, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cooled solution of 1-(3-aminophenyl)-3-(4-methoxybenzyl)-7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (synthesized according to General Procedure B) (200 mg) in dichloromethane (6 ml), triethylamine (0.08 ml, 0.59 mmol) was added followed by phenylsulphonyl chloride (0.08 ml, 0.59 mmol). The reaction mixture was warmed to room temperature and stirred for 2-3 hours. After completion of reaction (TLC, LCMS), the reaction mixture was diluted with dichloromethane (15 ml) and was washed with water (10 ml). The dichloromethane layer was dried over sodium sulfate and evaporated under reduced pressure. The crude compound was passed through a plug of silica (eluent 20% ethyl acetate in hexanes) and then purified by reverse phase HPLC on C-18 column to give N-(3-(3-(4-methoxybenzyl)-6,8-dioxo-7-phenethyl-3,6,7,8-tetrahydropyrazolo[3,4-b]pyrrolo[3,4-d]pyridin-1-yl)phenyl)benzenesulfonamide (45 mg, 18%) as a solid. 1HNMR (400 MHz, CDCl3): δ 9.04 (s, 1H), 7.83 (d, J=7.6 Hz, 2H), 7.56-7.20 (m, 14H), 6.84 (d, J=7.6 Hz, 2H), 6.57 (s, 1H), 5.73 (s, 2H), 3.91 (t, J=7.2 Hz, 2H), 3.76 (s, 3H), 2.96 (t, J=7.2 Hz, 2H); LCMS: [M+H] 643.

Workup

  1. customAfter completion of reaction (TLC, LCMS)
  2. washwas washed with water (10 ml)
  3. dry with materialThe dichloromethane layer was dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. custompurified by reverse phase HPLC on C-18 column

Sources & evidence

ORD record
ord-008b696ba2574fbaac72b068df3706ff
Source dataset
uspto-grants-2014_12
Patent number
US08906928B2

Reaction notes

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