Thiophenol → HCID 58465806, compound

HRID 1842465Notes

Reaction equation

HRID 1842465 reaction equation
[N+](C1C=CC=CC=1S([N:13]1[CH2:19][CH2:18][CH2:17][N:16]2[N:20]=[C:21]([C:23]([NH:25][O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[O:24])[CH:22]=[C:15]2[CH2:14]1)(=O)=O)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1>C(#N)C>[O:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:27]1[O:26][NH:25][C:23]([C:21]1[CH:22]=[C:15]2[CH2:14][NH:13][CH2:19][CH2:18][CH2:17][N:16]2[N:20]=1)=[O:24]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 58465654HCID 58465654, compound

Product 1

HCID 58465806HCID 58465806, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of 5-[(2-nitrophenyl)sulfonyl]-N-(tetrahydro-2H-pyran-2-yloxy)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxamide (0.15 g, 0.32 mmol) and cesium carbonate (0.2 g, 0.62 mmol) in acetonitrile (10 mL) was added a solution of benzenethiol (0.063 mL, 0.62 mmol) in acetonitrile (0.60 mL). The resulting reaction mixture was stirred at room temperature for 1 hour. The solvent was evaporated and the residue applied directly to silica purification (5% MeOH/DCM) to afford the title compound as a white solid (0.082 g, 91%). LC-MS: (FA) ES+281; 1H NMR (400 MHz, CDCl3) δ 6.59 (s, 1H), 5.30 (s, 1H), 5.08 (s, 1H), 4.39-4.32 (m, 2H), 4.08-4.00 (m, 1H), 3.92 (q, J=15.7 Hz, 2H), 3.71-3.61 (m, 1H), 3.26-3.15 (m, 2H), 2.29 (s, 1H), 1.92-1.79 (m, 5H), 1.70-1.54 (m, 3H).

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was evaporated
  3. customthe residue applied directly to silica purification (5% MeOH/DCM)

Sources & evidence

ORD record
ord-02e78dd585ed4d0ba81508d6d6113cfb
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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