Triethylamine → 3-(2,5-Dimethyl-benzenesulfonyl)-8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

HRID 1193137Notes

Reaction equation

HRID 1193137 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]3[CH:20]4[CH:15]([CH2:16][CH2:17][NH:18][CH2:19]4)[CH2:14]3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[S:29](Cl)(=[O:31])=[O:30].CCN(CC)CC>C(Cl)Cl>[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[S:29]([N:18]1[CH2:17][CH2:16][CH:15]2[CH:20]([N:13]([C:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:12]=[CH:11][N:10]=3)[CH2:14]2)[CH2:19]1)(=[O:30])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 87910Benzenesulfonyl chloride, 2,5-dimethyl-HCID 671167498-(4-Phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane2×

Product 1

HCID 529204073-(2,5-Dimethyl-benzenesulfonyl)-8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octaneYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane (Intermediate 6, 110 mg, 0.29 mmol), 2,5-dimethyl-benzenesulfonyl chloride (83 mg, 0.41 mmol) and Et3N (91 mg, 0.9 mmol) was stirred in DCM (5.0 mL) at RT for 18 h. The reaction mixture was diluted with more DCM (15 mL) and washed with water. The organic layers were combined, dried, filtered and concentrated under reduced pressure to yield crude product. The crude product was purified on HPLC (basic system) to yield the title compound (40 mg, 35%). MS (ESI) mass calcd. for C24H26N4O2S, 434.55; m/z found 435.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.26 (s br, 1H), 7.87 (s br, 2H), 7.70 (s, 1H), 7.51-7.34 (m, 3H), 6.94 (d, J=5.3, 1H), 6.91-6.73 (m, 2H), 4.62-4.52 (m, 1H), 4.16 (t, J=8.3, 1H), 4.04 (dd, J=13.5, 2.9, 1H), 3.93 (dd, J=8.6, 3.9, 1H), 3.85-3.73 (m, 1H), 3.74-3.59 (m, 1H), 3.40 (dd, J=13.5, 2.8, 1H), 2.95-2.89 (m, 1H), 2.45 (s, 3H), 2.28-2.12 (m, 1H), 2.21-1.85 (m, 4H).

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield crude product
  6. customThe crude product was purified on HPLC (basic system)

Sources & evidence

ORD record
ord-251f58e65e9945dfa7d815ffb8fcf897
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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