Methanesulfonyl chloride → HCID 67265929, compound

HRID 1685768Notes

Reaction equation

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

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 67265437HCID 67265437, compound

Product 1

HCID 67265929HCID 67265929, compoundYield 24.8%

Procedure

The title compound (3 mg) is prepared in analogy to Example 155 starting from 2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethylamine (10 mg, 27 μmol) and methanesulfonyl chloride (4 mg, 35 μmol); LC-MS: tR=0.78 min; [M+1]+=448.99; 1H NMR (CDCl3): δ 1.11 (t, J=7.0 Hz, 6H), 2.26 (s, 3H), 2.64 (q, J=7.3 Hz, 4H), 2.89 (s, 3H), 2.96-3.01 (m, 2H), 3.49 (q, J=6.8 Hz, 2H), 3.73 (s, 2H), 4.23 (t br, J=6.3 Hz, 1H), 7.37 (d, J=8.0 Hz, 2H), 7.67 (s, 1H), 8.13 (d, J=8.3 Hz, 2H).

Sources & evidence

ORD record: ord-1e00826bdd1548008cea879856b839cb
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148410B2

Reaction notes

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