Benzenesulfonyl chloride → HCID 11612496, compound

HRID 2221091Notes

Reaction equation

HRID 2221091 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=2)[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:3]1=[O:25].CCN(C(C)C)C(C)C.[C:35]1([S:41](Cl)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CC#N>[CH2:18]([N:4]1[C:5]2[C:10](=[CH:9][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][N:6]=2)[CH2:11][CH:2]([NH:1][S:41]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:43])=[O:42])[C:3]1=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58671553HCID 58671553, compound

Product 1

HCID 11612496HCID 11612496, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1J (120 mg, 0.36 mmol) in CH3CN (4 mL) at RT was added DIPEA (94 μL, 0.54 mmol), followed by benzenesulfonyl chloride (51 μL, 0.4 mmol). After 5 min, white precipitates formed. The reaction was stirred for additional 15 min. The product was collected by filtration and the solid washed with CH3CN (2-3 mL) to give the title compound as a white solid (100 mg, 71%). LC/MS (method A): retention time=3.96 min, (M+H)+=470. 1H NMR (CD3SOCD3, 400 MHz): δ8.60 (d, J=2.3 Hz, 1H), 8.35 (s, 1H), 7.07 (d, J=2.2 Hz, 1H), 7.94 (dd, J1=7.1 Hz, J2=1.5 Hz, 2H), 7.70 (dd, J1=8.5 Hz, J2=1.3 Hz, 2H), 7.66-7.69 (m, 1H), 7.61-7.64 (m, 2H), 7.54 (t, J =7.5 Hz, 2H), 7.34-7.46 (m, 1H), 7.25 -7.34 (m, 5H), 5.16 (dd, J1=47.0 Hz, J2=15.2 Hz, 2H), 4.44-4.50 (m, 1H), 3.20 (dd, J1=15.9 Hz, J2=6.0 Hz), 3.06-3.13 (m, 1H).

Workup

  1. customwhite precipitates
  2. customformed
  3. filtrationThe product was collected by filtration
  4. washthe solid washed with CH3CN (2-3 mL)

Sources & evidence

ORD record
ord-b1443d4dffbb448984ee47d961cfee77
Source dataset
uspto-grants-2008_05
Patent number
US07368458B2

Reaction notes

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