Dichloromethane → HCID 11301851, compound

HRID 495134Notes

Reaction equation

HRID 495134 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16](=[O:18])[CH:15]=[C:14]([O:19][CH2:20][CH2:21][CH2:22][NH:23][CH3:24])[C:13]=2[CH:25]=1.C(Cl)Cl.CC[N:31]([CH:35](C)C)C(C)C.CN=C=[S:41]>CN(C=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16](=[O:18])[CH:15]=[C:14]([O:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([NH:31][CH3:35])=[S:41])[C:13]=2[CH:25]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11167Methyl isothiocyanateHCID 81531DiisopropylethylamineHCID 86596924HCID 86596924, compound

Product 1

HCID 11301851HCID 11301851, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt (0.272 mmol, 100 mg) is suspended in 5 mL of 1:1 DMF:DCM. DIEA is added dropwise until pH=9 by pH paper. Methyl isothiocyanate (0.299 mmol, 0.022 g) is added and the reaction is stirred at ambient temperature for 3 hrs. The reaction mixture is concentrated in vacuo and the crude material is purified by reversed-phase HPLC to afford the title compound (66.1 mg, 78.7%). 1H NMR (DMSO-d6, 300 MHz) δ 7.85 (1H, d, J=2.5 Hz), 7.71 (1H, dd, J=2.75, 9 Hz), 7.55 (1H, br m), 7.46 (1H, d, J=9 Hz), 5.95 (1H, s), 4.24 (2H, t, J=5.75 Hz), 3.59 (2H, br s), 2.79 (3H, br s), 2.07 (2H, m); MS (ESI, Pos.) calcd for C14H15ClN2O3S m/z [M+H]=327.0, found 327.0.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe crude material is purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-cbecee1295a442f49b0457fc190e6e30
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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