Triphenylphosphine → 4-{[1-(1-Benzenesulfonyl-pyrrolidin-3-yl)-5-oxo-4,4-bis-pyridin-4-ylmethyl-imidazolidin-2-ylidene]-acetyl}-benzonitrile

HRID 636809Notes

Reaction equation

HRID 636809 reaction equation
[C:1]1([S:7]([N:10]2[CH2:14][CH2:13][CH:12]([N:15]=[C:16]=O)[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[C:20](=[O:37])[C:21]([NH2:36])([CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.[S].[C:39]([C:41]1[CH:50]=[CH:49][C:44]([C:45](=[O:48])[CH2:46]Br)=[CH:43][CH:42]=1)#[N:40].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:1]1([S:7]([N:10]2[CH2:14][CH2:13][CH:12]([N:15]3[C:20](=[O:37])[C:21]([CH2:22][C:23]4[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=4)([CH2:29][C:30]4[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=4)[NH:36][C:16]3=[CH:46][C:45]([C:44]3[CH:49]=[CH:50][C:41]([C:39]#[N:40])=[CH:42][CH:43]=3)=[O:48])[CH2:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 6

HCID 11776TriphenylphosphineHCID 986544-(Bromoacetyl)benzonitrileHCID 3251421Potassium bis(trimethylsilyl)amide2×HCID 5362487Sulfur2×HCID 15462778HCID 15462778, compound2×HCID 212553501-Phenylsulfonylpyrrolidin-3-ylisocyanate

Product 1

HCID 702247534-{[1-(1-Benzenesulfonyl-pyrrolidin-3-yl)-5-oxo-4,4-bis-pyridin-4-ylmethyl-imidazolidin-2-ylidene]-acetyl}-benzonitrile

Procedure

Using the same procedure as described in Example 1, 1 -phenylsulfonylpyrrolidin-3-ylisocyanate (1.38 mmol) was used in the place of 3-benzenesulfonyl-6-isothiocyanato-3-aza-bicyclo[3.1.0]hexane. After cyclization with 2-amino-3-pyridin-4-yl-2-pyridin-4-ylmethyl-propionic acid methyl ester (1.10 mmol) as described in 1B, sulfur-alkylation of 4-cyanophenacyl bromide in the presence of potassium bis(trimethylsilyl)amide as described in 1C and sulfur-extrusion in the presence of triphenylphosphine as described in 1D, 40 mg of the title compound was obtained as a white solid.

Sources & evidence

ORD record
ord-fce59364d654475a95caf865fda7266a
Source dataset
uspto-grants-2001_02
Patent number
US06194438B1

Reaction notes

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