Cesium carbonate → HCID 21896663, compound

HRID 719108Notes

Reaction equation

HRID 719108 reaction equation
[O:1]=[S:2]1(=[O:30])[C:8]2[CH:9]=[C:10]([O:14][CH3:15])[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][C:4]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[NH:3]1.[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Cl)=[CH:35][CH:34]=1.[I-].[Cs+].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[O:30]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:14][CH3:15])[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][C:4]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[N:3]1[CH2:37][C:36]1[CH:39]=[CH:40][C:33]([O:32][CH3:31])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 24601Cesium iodideHCID 699934-Methyloxybenzyl chlorideHCID 21896720HCID 21896720, compound

Product 1

HCID 21896663HCID 21896663, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1,1-dioxo-3,3-dibutyl-5-phenyl-7-bromo-8-methoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (prepared according to WO 98/38182; 0.200 g, 0.404 mmol) in MeCN (5 ml) where added p-methoxybenzyl chloride (0.066 ml, 0.486 mmol), CsI (0.010 g, 0.038 mmol) and Cs2CO3 (0.263 g, 0.807 mmol) and the mixture was stirred at 60° C. for 4 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and 0.5M HCl (aq). The organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was filtered through silica gel (DCM:EtOAc-9:1) to give the title compound in 0.257 g (˜quant) as an off-white solid. NMR (400 MHz, CDCl3): 0.60–0.75 (m, 6H), 0.75–1.20 (m, 8H), 1.25–1.45 (m, 2H), 1.80–2.00 (m, 2H), 3.80 (s, 3H), 3.90 (s, 3H), 4.05–4.30 (m, 2H), 4.45–4.65 (m, 2H), 6.70–7.45 (m, 11H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and 0.5M HCl (aq)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. filtrationThe residue was filtered through silica gel (DCM:EtOAc-9:1)

Sources & evidence

ORD record
ord-12f510ee0a4c473f8bdcc0850a08571e
Source dataset
uspto-grants-2006_11
Patent number
US07132416B2

Reaction notes

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