P-Toluenesulfonamide → N-4-Tolylsulphonyl-2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)-phenyl]-2-cyclopentyl-acetamide

HRID 1955738Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]([OH:23])=O)=[CH:16][CH:15]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.S(Cl)(C)(=O)=O.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47]([NH2:50])(=[O:49])=[O:48])=[CH:43][CH:42]=1>C1COCC1.CN(C1C=CN=CC=1)C.O.C(O)(=O)C>[C:41]1([CH3:51])[CH:42]=[CH:43][C:44]([S:47]([NH:50][C:21](=[O:23])[CH:20]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][N:6]3[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=[C:5]3[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:15][CH:16]=2)[CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)(=[O:48])=[O:49])=[CH:45][CH:46]=1

Participants

Conditions

Temperature: 25 °C

Procedure

1.2 g (2.6 mmol) of the compound from Example II are dissolved in 30 ml of THF, then 0.72 mol (5.2 mmol) of triethylamine, 0.23 ml (2.9 mmol) of mesyl chloride, 320 mg (2.6 mmol) of DMAP and 535 mg (3.1 mmol) of 4-tolylsulphonamide in 10 ml of THF are added successively at 0° C. The mixture is stirred at 25° C. for 20 h, 0.4 ml of glacial acetic acid and 30 ml of water are added, the mixture is extracted three times with 30 ml of ethyl acetate, the organic is phase is concentrated and the residue is chromatographed on silica gel 60 using dichloromethane/methanol (100:2).

Workup

extractionthe mixture is extracted three times with 30 ml of ethyl acetate
concentrationis concentrated
customthe residue is chromatographed on silica gel 60 using dichloromethane/methanol (100:2)

Sources & evidence

ORD record: ord-f151113adc7b4ece8ace9894caf5cc18
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05776964

Reaction notes

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