Sodium Carbonate → HCID 86697032, compound

HRID 1525680Notes

Reaction equation

HRID 1525680 reaction equation
B(Br)(Br)Br.[CH3:5][NH:6][C:7](=[O:38])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]([CH3:22])([CH2:19][O:20]C)[C:17](=[O:23])[N:16]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=3)[C:15]2=[S:36])=[CH:10][C:9]=1[F:37].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:5][NH:6][C:7](=[O:38])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]([CH2:19][OH:20])([CH3:22])[C:17](=[O:23])[N:16]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=3)[C:15]2=[S:36])=[CH:10][C:9]=1[F:37]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromide2×HCID 56649280HCID 56649280, compound

Product 1

HCID 86697032HCID 86697032, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

BBr3 (53 mkl, 0.55 mmol) was added dropwise to solution of N-methyl-4-[5-methyl-5-(methoxymethyl)-4-oxo-2-thioxo-3-[3-(trifluoromethyl)-4-cyanophenyl]imidazolidin-1-yl]-2-fluorobenzamide (55 mg, 0.11 mmol) in CH2Cl2 (1.5 ml) in argon atmosphere at −78° C. The reaction mixture was stirred at −78° C. for 3 h and then for another 3 h at room temperature. After the reaction was completed the excess of BBr3 was neutralized by addition of 5% Na2CO3 solution (10 ml), the product was extracted with AcOEt, dried over Na2SO4, evaporated in vacuo, and by HPLC method N-methyl-4-[5-(hydroxymethyl)-5-methyl-4-oxo-2-thioxo-3-[3-(trifluoromethyl)-4-cyanophenyl]imidazolidin-1-yl]-2-fluorobenzamide 1.2.2(3) was isolated, Ki1.2.2(3)=46.3 nM, 1H NMR (DMSO-d6, 400 MHz): 8.43 (br. m, 1H), 8.39 (d, J=8.4 Hz, 1H), 8.13 (s, 1H), 7.98 (d, J=8.4 Hz, 1H), 7.78 (t, J=8.0 Hz, 1H), 7.42 (d, J=10.8 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H), 5.93 (t, J=4.4 Hz, 1H), 3.81 (dd, J1=11.6 Hz, J2=4.4 Hz, 1H), 3.45 (dd, J1=11.6 Hz, J2=5.0 Hz, 1H), 2.79 (d, J=4.0 Hz, 3H), 1.38 (s, 3H).

Workup

  1. waitfor another 3 h at room temperature
  2. extractionthe product was extracted with AcOEt
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customwas isolated

Sources & evidence

ORD record
ord-8b0cc592e0ee48fbb1e030fee2346f45
Source dataset
uspto-grants-2015_07
Patent number
US09085539B2

Reaction notes

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