Sulfuryl chloride → (R)-7-Chloro-2,3,4,5-tetrahydro-4-(ethenylsulfonyl)-3-(phenylmethyl)-1H-1,4-benzodiazepine

HRID 849421Notes

Reaction equation

[ClH:1].Cl.Cl.N1C=C(CN2C3C=CC(C4C=NC=CC=4)=CC=3CN(C(=O)C(F)(F)F)C(CC3C=CC=CC=3)C2)N=[CH:5]1.CCN(C(C)C)C(C)C.S(Cl)(Cl)(=O)=O.C([C:56]1[CH:57]=[CH:58][C:59]2[N:65](CC3N=CN(C(OC(C)(C)C)=O)C=3)[CH2:64][C@@H:63]([CH2:79][C:80]3[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=3)[N:62]([S:86]([CH3:89])(=[O:88])=[O:87])[CH2:61][C:60]=2[CH:90]=1)#N>C(Cl)Cl>[Cl:1][C:56]1[CH:57]=[CH:58][C:59]2[NH:65][CH2:64][C@@H:63]([CH2:79][C:80]3[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=3)[N:62]([S:86]([CH:89]=[CH2:5])(=[O:88])=[O:87])[CH2:61][C:60]=2[CH:90]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4.4g (16.1 mmol) of Compound B of Example 347 in 75 ml of methylene chloride, at -78° C. and under argon, was added dropwise approximately one-half of a solution of 2.5 ml (24.2 mmol) of 2-chlorosulfonyl chloride in 15 ml of methylene chloride. Then was added rapidly dropwise 5 ml of DIPEA, followed by the remaining sulfonyl chloride solution and an additional 2.4 ml of DIPEA (total 7.4 ml, 40.3 mmol). The resulting pale yellow solution was stirred at -78° C. for 0.5 hr, allowed to warm to rt and reduced to one-half volume. The solution of crude Compound A was used directly.

Workup

temperatureto warm to rt

Sources & evidence

ORD record: ord-f386a15245f54fbd801e671cd16701fd
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011029

Reaction notes

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