Trityl chloride → (r)-2,3,4,5-Tetrahydro-1-(1-(triphenylmethyl)-imidazol-4-ylmethyl)-4-(methylsulfonyl)-3-(phenylmethyl)-1h-1,4-benzodiazepine-7-carbonitrile

HRID 1282700Notes

Reaction equation

HRID 1282700 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][N:8]2[C:14]3[CH:15]=[CH:16][C:17]([C:19]#[N:20])=[CH:18][C:13]=3[CH2:12][N:11]([S:21]([CH3:24])(=[O:23])=[O:22])[C@H:10]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:9]2)[N:4]=[CH:3]1.[C:32]1([C:38](Cl)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C>[C:32]1([C:38]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[N:2]2[CH:6]=[C:5]([CH2:7][N:8]3[C:14]4[CH:15]=[CH:16][C:17]([C:19]#[N:20])=[CH:18][C:13]=4[CH2:12][N:11]([S:21]([CH3:24])(=[O:22])=[O:23])[C@H:10]([CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:9]3)[N:4]=[CH:3]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 178504922HCID 178504922, compound

Product 1

HCID 69842016(r)-2,3,4,5-Tetrahydro-1-(1-(triphenylmethyl)-imidazol-4-ylmethyl)-4-(methylsulfonyl)-3-(phenylmethyl)-1h-1,4-benzodiazepine-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.2 g (2.85 mmol) of the free base of Example 225 in 20 ml of acetonitrile, at rt and under argon, was added 1.2 ml (8.55 mmol) of TEA, followed by 1.2 g (4.3 mmol) of triphenylmethyl chloride. Stirring was continued overnight. The resulting cloudy solution was evaporated to dryness and the residue subjected to flash chromatography on a 100 cc column of silica gel (50% ethyl acetate-hexane) to afford 1.2 g (64%) of Cmpd A as a viscous white foam.

Workup

  1. customThe resulting cloudy solution was evaporated to dryness
  2. customto afford 1.2 g (64%) of Cmpd A as a viscous white foam

Sources & evidence

ORD record
ord-1c6e8e223c9944e686e1f74d531d1ebc
Source dataset
uspto-grants-2002_09
Patent number
US06455523B1

Reaction notes

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