Pyridine-2-sulfonyl Chloride → tert-butyl(3R)-6-cyclohexyl-3-(3-{[(2-pyridinylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

HRID 2084449Notes

Reaction equation

HRID 2084449 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:5][N:4]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33]>>[CH:20]1([CH2:19][CH2:18][CH2:17][C@@H:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][NH:1][S:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=3)(=[O:34])=[O:33])[N:7]=2)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 3787675Pyridine-2-sulfonyl ChlorideHCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

Product 1

HCID 16748331tert-butyl(3R)-6-cyclohexyl-3-(3-{[(2-pyridinylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

Procedure

Method same as for preparation 10 using tert-butyl (3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate (preparation 18) (210 mg, 057 mmol) and 2-pyridinesulphonylchloride (J. Med. Chem; 1997, 40, 1149) (170 mg, 0.96 mmol) as starting materials.

Sources & evidence

ORD record
ord-662b32111cd24e6aace7032ca30f4847
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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