Benzenesulfonyl chloride → (R)-7-Chloro-2,3,4,5-tetrahydro--[(1-methyl-1H-imidazol-5-yl)methyl]-4-(phenylsulfonyl)-3-(phenylmethyl)-1H-1,4-benzodiazepine, monohydrochloride

HRID 849419Notes

Reaction equation

HRID 849419 reaction equation
[ClH:1].Cl.Cl.[NH:4]1[CH:8]=[C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][C:19](C4C=NC=CC=4)=[CH:20][C:15]=3[CH2:14][N:13](C(=O)C(F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)[N:6]=[CH:5]1.[C:40](C1C=CC2NC[C@@H](CC3C=CC=CC=3)N(C(=O)CC3C=CC=CC=3)CC=2C=1)#N.[C:69]1([S:75]([Cl:78])(=[O:77])=[O:76])[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1.[H-]>>[ClH:78].[Cl:1][C:19]1[CH:18]=[CH:17][C:16]2[N:10]([CH2:9][C:7]3[N:6]([CH3:40])[CH:5]=[N:4][CH:8]=3)[CH2:11][C@@H:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:13]([S:75]([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)(=[O:77])=[O:76])[CH2:14][C:15]=2[CH:20]=1

Participants

5

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 166653HydrideHCID 53636257(R)-7-cyano-2,3,4,5-tetrahydro-4-(phenylacetyl)-3-(phenylmethyl)-1H-1,4-benzodiazepineHCID 178478619HCID 178478619, compound

Product 1

HCID 131721598(R)-7-Chloro-2,3,4,5-tetrahydro--[(1-methyl-1H-imidazol-5-yl)methyl]-4-(phenylsulfonyl)-3-(phenylmethyl)-1H-1,4-benzodiazepine, monohydrochloride

Procedure

Example 249 was prepared as a light yellow solid from Compound B of Example 247 by the following sequence: Compound C of Example 247, with benzenesulfonyl chloride, with stirring at rt for 3 hours and chromatography on silica with 7/3 hexanes/EtOAc (57 %); Compound D of Example 247, with stirring at rt for 12 hours and with stirring for 2 days following addition of another equivalent of hydride and aldehyde, and with purification by reverse phase HPLC (gradient of aqueous methanol with 0.1% TFA; 52%). MS (M+H)+ =507.

Workup

  1. customwith purification by reverse phase HPLC (gradient of aqueous methanol with 0.1% TFA; 52%)

Sources & evidence

ORD record
ord-9a021294623e4646b73b3effcf7554f8
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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