Methanesulfonyl chloride → 4-(adamantan-1-ylmethoxy)-3-cyclopropyl-N-(N,N-dimethylsulfamoyl)benzamide

HRID 1849504Notes

Reaction equation

HRID 1849504 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][C:14]=3[C:22]3C(OC)=NC=[CH:26][CH:27]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C12(COC3C=CC(C(N)=O)=CC=3C3CC3)CC3CC(CC(C3)C1)C2.CS(Cl)(=O)=O.[CH3:59][N:60]([CH3:65])[S:61](Cl)(=[O:63])=[O:62]>>[C:1]12([CH2:11][O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH:19][S:61](=[O:63])(=[O:62])[N:60]([CH3:65])[CH3:59])=[O:18])=[CH:15][C:14]=3[CH:22]3[CH2:26][CH2:27]3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

5

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 83372Dimethylsulphamoyl chlorideHCID 867028454-(Adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamideHCID 867028484-(Adamantan-1-ylmethoxy)-3-cyclopropylbenzamide

Product 1

HCID 867028494-(adamantan-1-ylmethoxy)-3-cyclopropyl-N-(N,N-dimethylsulfamoyl)benzamide

Procedure

Following the procedure as described in Example 38 step 4 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamide with 4-(adamantan-1-ylmethoxy)-3-cyclopropylbenzamide and methanesulfonyl chloride with dimethylsulfamoyl chloride, the title compound was obtained as a colorless solid (0.19 g, 34%): 1H NMR (300 MHz, CDCl3) δ 8.65 (br s, 1H), 7.64-7.56 (m, 1H), 7.41-7.35 (m, 1H), 6.85-6.77 (m, 1H), 3.57 (s, 2H), 3.01 (s, 6H), 2.19-2.08 (m, 1H), 2.02 (br s, 3H), 1.79-1.58 (m, 12H), 0.99-0.91 (m, 2H), 0.71-0.64 (m, 2H); MS (ES−) m/z: 431.2 (M−1).

Sources & evidence

ORD record
ord-f8743912c67b4ad28d7c4e0139e9f026
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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