Dimethylsulphamoyl chloride → Rac-n-(3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-2-hydroxy-propyl)-sulfamic acid dimethyl-amide

HRID 1685773Notes

Reaction equation

[NH2:1][CH2:2][CH:3]([OH:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[S:17][C:18]([CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[C:19]([CH3:21])[CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1.[CH3:29][N:30]([CH3:35])[S:31](Cl)(=[O:33])=[O:32]>>[CH3:29][N:30]([CH3:35])[S:31](=[O:33])(=[O:32])[NH:1][CH2:2][CH:3]([OH:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[S:17][C:18]([CH2:22][N:23]([CH2:24][CH3:25])[CH2:26][CH3:27])=[C:19]([CH3:21])[CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 83372Dimethylsulphamoyl chloride

HCID 67265790Rac-1-amino-3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propan-2-ol

Product 1

HCID 67265838Rac-n-(3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-2-hydroxy-propyl)-sulfamic acid dimethyl-amideYield 33.1%

Procedure

The title compound (21 mg) is prepared in analogy to Example 166 starting from rac-1-amino-3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propan-2-ol (50 mg, 125 μmol) and dimethylsulfamoyl chloride (22 mg, 150 μmol); LC-MS: tR=0.76 min; [M+1]+=508.18; 1H NMR (CDCl3): δ1.11 (t, J=7.0 Hz, 6H), 2.25 (s, 3H), 2.64 (q, J=7.0 Hz, 4H), 2.83 (s, 6H), 2.85-2.94 (m, 2H), 3.03-3.10 (m, 1H), 3.24-3.30 (m, 1H), 3.73 (s, 2H), 4.04-4.11 (m, 1H), 7.37 (d, J=8.3 Hz, 2H), 7.66 (s, 1H), 8.10 (d, J=8.3 Hz, 2H).

Sources & evidence

ORD record: ord-66356517b59c48debc94797f41cae3a6
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148410B2

Reaction notes

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