Potassium Carbonate → HCID 88410086, compound

HRID 1439947Notes

Reaction equation

HRID 1439947 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH2:15]CS([O-])(=O)=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[ClH:22].[F:23][C:24]([F:57])([F:56])[C:25]1[CH:26]=[C:27]([CH2:35][O:36][C@@H:37]2[CH2:42][CH2:41][CH2:40][N:39](CC3C=[NH+]C=CC=3)[C@@H:38]2[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[ClH:22].[ClH:22].[F:33][C:31]([F:32])([F:34])[C:29]1[CH:28]=[C:27]([CH2:35][O:36][C@H:37]2[CH2:42][CH2:41][CH2:40][N:39]([CH2:15][C:11]3[N:10]([S:7]([C:4]4[CH:5]=[CH:6][C:1]([CH3:21])=[CH:2][CH:3]=4)(=[O:9])=[O:8])[CH:14]=[CH:13][N:12]=3)[C@H:38]2[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:26]=[C:25]([C:24]([F:57])([F:23])[F:56])[CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 131719281HCID 131719281, compoundHCID 131719282HCID 131719282, compound

Product 1

HCID 88410086HCID 88410086, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

((N-p-Toluenesulfonyl)imidazol-2-yl)methylmethanesulfonate (1.6 g) was added to a suspension of the compound of Description 3 (2.47 g) and potassium carbonate (800 mg) in dimethylformamide (10 ml) and the resulting mixture was heated at 100° C. for 2 h. The mixture was cooled, diluted with water (100 ml) and extracted with ethyl acetate (3×20 ml). The organic extracts were combined, washed with brine, dried (MgSO4) and concentrated in vacuo. This afforded a colourless oil which was purified by column chromatography on silica using 25-30% ethyl acetate in hexane. This afforded the product as a white crystalline solid which was recrystallised from dichloromethane/petrol: mp 125°-126° C. 1H NMR (360 MHz, DMSO-d6) d 1.4-1.5 (1H, m, NCH2CH2CHH), 1.5-1.67 (1H, m, NCH2CH2CHH), 1.8-2.0 (1H, m, NCH2CHH), 2.06-2.1 (1H, m, NCH2CHH), 2.35 (3H, s, CH3), 2.4 (1H, mc, NCHH), 2.7-2.86 (1H, m, NCHH), 3.50 (1H, d, J=14.0 Hz, CHH-imidazole), 3.56 (1H, brs, CHO), 3.76 (1H, d, J=1.5 Hz, CHPh), 4.08 (1H, d, J=14.0 Hz, CHH-imidazole), 4.09 (1H, d, J=12.0 Hz, OCHH), 4.48 (1H, d, J=12.0 Hz, OCHH), 6.96 (1H, d, J=1.0 Hz, imidazole-H), 7.12 (2H, d, J=8.5 Hz, ArH), 7.2-7.3 (3H, m, ArH), 7.34 (1H, d, J=1.0 Hz, imidazole-H), 7.46-7.58 (2H, m, ArH), 7.60 (2H, s, ArH), 7.71 (1H, ArH), 7.79 (2H, d, J=8.5 Hz, ArH); MS (CI+) m/z 638 (M+ +1). Found: C, 58.48; H, 4.78; N, 6.72; S, 4.81. Calcd. for C31H29F6N3O3S: C, 58.39; H, 4.58; N, 6.59; S, 5.03%.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThis afforded a colourless oil which
  7. customwas purified by column chromatography on silica using 25-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1bf709505f67458abe74dcf9b9c4cbde
Source dataset
uspto-grants-1996_03
Patent number
US05496833

Reaction notes

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