Dimethylformamide → HCID 57718196, compound

HRID 1366832Notes

Reaction equation

HRID 1366832 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([SH:10])[CH2:8][CH3:9].CN(C=O)C.[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[S:24]([NH:27][C:28]1[N:33]=[C:32](Cl)[C:31]([S:35][C:36]2[CH:41]=[CH:40][C:39]([S:42]([N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)(=[O:44])=[O:43])=[CH:38][CH:37]=2)=[CH:30][N:29]=1)(=[O:26])=[O:25]>CC(C)=O>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[S:24]([NH:27][C:28]1[N:33]=[C:32]([S:10][CH2:7][CH2:8][CH3:9])[C:31]([S:35][C:36]2[CH:37]=[CH:38][C:39]([S:42]([N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)(=[O:44])=[O:43])=[CH:40][CH:41]=2)=[CH:30][N:29]=1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7848Propyl mercaptanHCID 10796Cesium carbonateHCID 57718206HCID 57718206, compound

Product 1

HCID 57718196HCID 57718196, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Cesium carbonate (65 mg, 0.2 mmol) was added to a solution of propanethiol (8 μl, 0.09 mmol) in acetone (0.5 mL). The reaction mixture was heated to 50° C. for 45 minutes then cooled to r.t. DMF (2 mL) and 2,4-Dichloro-N-{4-chloro-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-pyrimidin-2-yl}-benzenesulfonamide 11 (50 mg, 0.08 mmol) were added and the resultant mixture heated to 50° C. for 2 hours. The reaction was allowed to cool, filtered through celite and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (2% MeOH in DCM) to afford 2,4-Dichloro-N-{5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-4-propylsulfanyl-pyrimidin-2-yl}-benzenesulfonamide 32 (20 mg). 1H NMR (CDCl3): δ 1.00 (m, 3H), 1.27 (m, 2H), 1.66 (m, 6H), 2.88 (m, 2H), 2.99 (m, 4H), 7.26 (m, 2H), 7.45 (d, 1H), 7.55 (s, 1H), 7.66 (d, 2H), 8.27 (d, 1H), 8.5149 (s, 1H), 12.61 (br s, 1H) ppm. Mass Spectrum m/e=632.8 (M+1).

Workup

  1. temperaturethen cooled to r.t
  2. temperatureto cool
  3. filtrationfiltered through celite
  4. customthe solvent evaporated in vacuo
  5. customThe crude product was purified by flash column chromatography (2% MeOH in DCM)

Sources & evidence

ORD record
ord-4d9dab96d02c485789e240083544d546
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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