Chlorosuccinimide → HCID 59625695, compound

HRID 1911167Notes

Reaction equation

HRID 1911167 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([N:19]4[CH2:22][CH:21]([N:23]5[CH2:28][CH2:27][N:26]([C:29]([C:31]6[S:32][CH:33]=[CH:34][N:35]=6)=[O:30])[CH2:25][CH2:24]5)[CH2:20]4)=[O:18])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:43])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:43][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([C:17]([N:19]3[CH2:20][CH:21]([N:23]4[CH2:28][CH2:27][N:26]([C:29]([C:31]5[S:32][CH:33]=[CH:34][N:35]=5)=[O:30])[CH2:25][CH2:24]4)[CH2:22]3)=[O:18])[CH:12]=2)[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 59625954HCID 59625954, compound

Product 1

HCID 59625695HCID 59625695, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Cpd 487 (0.2 mmol, 100 mg) in CCl4 (4 mL) and CH2Cl2 (4 mL) was added NCS (0.25 mmol, 33 mg). The reaction mixture was stirred at room temperature for 4 h. It was then diluted with CH2Cl2 and washed with 1N aqueous NaOH and H2O, dried over Na2SO4, and concentrated. Purification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2) gave 51 mg of Cpd 1365. MS m/z (M+H+) 524.

Workup

  1. washwashed with 1N aqueous NaOH and H2O
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2)
  5. customgave 51 mg of Cpd 1365

Sources & evidence

ORD record
ord-4b7f8341e6234aefa5aba4c0265d814b
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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