Chlorosuccinimide → HCID 22050966, compound

HRID 1867086Notes

Reaction equation

HRID 1867086 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:11]=1[CH2:12][NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]([CH2:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[C:25]#[N:26])[C:16](=[O:30])[CH:15]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:15]1[C:16](=[O:30])[N:17]([CH2:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[C:25]#[N:26])[C:18]([CH3:20])=[CH:19][C:14]=1[NH:13][CH2:12][C:11]1[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:10]=1[F:9]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 22050269HCID 22050269, compound

Product 1

HCID 22050966HCID 22050966, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chloro succinimide (36 mg, 0.27 mmol) was added to a solution of the product of Step 5 (0.125 g, 0.26 mmol) in methylene chloride (10 mL). After stirring at 25 C for 2 h, the reaction was complete by LC-MS. The reaction mixture was poured into saturated aqueous NaHCO3. The aqueous mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The residue was triturated with acetonitrile to give the title compound as a tan solid (20 mg, 13%). 1H NMR (400 MHz, CD3OD) δ 7.61 (d, J=8.4 Hz, 1H), 7.49 (m, 2H), 7.40 (d, J=8.4 Hz, 1H), 7.33 (q, J=8.4 and 14.8 Hz, 1H), 6.94 (m, 2H), 6.00 (s, 1H), 5.34 (s, 2H), 4.56 (s, 2H), 2.21 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ −114.00 (1F), −116.89 (1F) ppm. LC/MS, tr=5.49 minutes (5 to 95% acetonitrile/water over 8 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-MS m/z 400 (M+H).

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-e93e9195bf444081abab730745b1480a
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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