Dichloromethane → HCID 68568015, compound

HRID 1990919Notes

Reaction equation

HRID 1990919 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:14]2[N:15]=[C:16]([NH:31][CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])[C:17]3[CH:22]=[C:21]([CH2:23][O:24][CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[NH:20][C:18]=3[N:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCN(CC)CC.C(Cl)Cl.[C:48]([C:50]1[CH:55]=[CH:54][C:53]([S:56](Cl)(=[O:58])=[O:57])=[CH:52][CH:51]=1)#[N:49]>C1COCC1>[C:48]([C:50]1[CH:51]=[CH:52][C:53]([S:56]([CH:23]([O:24][CH:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]2)[C:21]2[NH:20][C:18]3[N:19]=[C:14]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:15]=[C:16]([NH:31][CH2:32][CH2:33][NH:34][C:35](=[O:37])[CH3:36])[C:17]=3[CH:22]=2)(=[O:58])=[O:57])=[CH:54][CH:55]=1)#[N:49]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 68566227HCID 68566227, compound

Product 1

HCID 68568015HCID 68568015, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Amine 14 (62 mg) and NEt3 (0.1 mL) were stirred in THF (6 mL) and DCM (6 mL) and cooled to 5° C. 4-Cyanophenylsulfonyl chloride (30 mg) was added dropwise by syringe, and stirring was continued at rt for 2 h, then the reaction mixture was concentrated. The residue was redissolved in DCM and washed with saturated NaHCO3, brine, and dried over MgSO4. After removal of solvent, the crude product was purified by preparative TLC (silica gel, DCM/MeOH=12/1) to give 16 mg (36%) of 15.3 as an off-white foam. 1H-NMR (200 MHz, CDCl3): δ 1.50-1.67 (m, 2H), 1.80 (s, 3H), 2.94-3.20 (m, 4H), 3.32-3.46 (m, 1H), 3.50-3.70 (m, 2H), 3.80-3.95 (m, 2H), 4.47 (s, 2H), 5.72 (brs, 1H), 6.22 (s, 1H), 6.81 (brs, 1H), 7.20-7.38 (m, 3H), 7.75-7.90 (m, 4H), 8.37-8.40 (m, 2H), 9.37 (brs, 1H); MS (ES): 574.1 [MH+].

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was redissolved in DCM
  3. washwashed with saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. customAfter removal of solvent
  6. customthe crude product was purified by preparative TLC (silica gel, DCM/MeOH=12/1)

Sources & evidence

ORD record
ord-162cfca925b6499a9838414f6cb23a25
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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