4-(Bromoacetyl)benzonitrile → 4-{[1-(3-Benzenesulfonyl-3-aza-bicyclo[3.1.0]hex-6-yl)-4,4-bis-(1-trityl-1H-imidazol-4-ylmethyl)-4,5-dihydro-5-oxo-1H-imidazol-2-ylsulfanyl]-acetyl}-benzonitrile

HRID 636815Notes

Reaction equation

HRID 636815 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH:14]3[CH:12]([CH:13]3[N:16]3[C:20](=[O:21])[C:19]([CH2:47][C:48]4[N:49]=[CH:50][N:51]([C:53]([C:66]5[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=5)([C:60]5[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=5)[C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)[CH:52]=4)([CH2:22][C:23]4[N:24]=[CH:25][N:26]([C:28]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH:27]=4)[NH:18][C:17]3=[S:72])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:73]([C:75]1[CH:84]=[CH:83][C:78]([C:79](=[O:82])[CH2:80]Br)=[CH:77][CH:76]=1)#[N:74].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>>[C:1]1([S:7]([N:10]2[CH2:15][CH:14]3[CH:12]([CH:13]3[N:16]3[C:20](=[O:21])[C:19]([CH2:47][C:48]4[N:49]=[CH:50][N:51]([C:53]([C:60]5[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=5)([C:66]5[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=5)[C:54]5[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=5)[CH:52]=4)([CH2:22][C:23]4[N:24]=[CH:25][N:26]([C:28]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH:27]=4)[N:18]=[C:17]3[S:72][CH2:80][C:79]([C:78]3[CH:83]=[CH:84][C:75]([C:73]#[N:74])=[CH:76][CH:77]=3)=[O:82])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 3251421Potassium bis(trimethylsilyl)amideHCID 882180533-(3-Benzenesulfonyl-3-aza-bicyclo[3.1.0]hex-6-yl)-2-thioxo-5,5-bis-(1-trityl-1H-imidazol-4-ylmethyl)-imidazolidin 4one

Product 1

HCID 882180794-{[1-(3-Benzenesulfonyl-3-aza-bicyclo[3.1.0]hex-6-yl)-4,4-bis-(1-trityl-1H-imidazol-4-ylmethyl)-4,5-dihydro-5-oxo-1H-imidazol-2-ylsulfanyl]-acetyl}-benzonitrile

Procedure

Using the same procedure as described in Example 1C, the title compound of 53C (0.548 g, 0.558 mmol) and 4-cyanophenacyl bromide (138 mg, 0.614 mmol) in the presence of potassium bis(trimethylsilyl)-amide (129 mg, 0.614 mmol) reacted to yield the title compound of 53D, after chromatographic purification, 0.46 g (0.41 mmol, 73% yield).

Sources & evidence

ORD record
ord-9122f055859148baa9fe44728ab7cce2
Source dataset
uspto-grants-2001_02
Patent number
US06194438B1

Reaction notes

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