Methanesulfonamide → 4-(adamantan-2-yl(benzyloxy)methyl)-3-chloro-N-(methylsulfonyl)benzamide

HRID 1849752Notes

Reaction equation

HRID 1849752 reaction equation
C12(COC3C(I)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[CH:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH:25]1[CH:34]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:35]1[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][C:36]=1[Cl:44])[CH2:31]2.N1(S(N)(=O)=O)CCC1.[CH3:61][S:62]([NH2:65])(=[O:64])=[O:63]>>[CH:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH:25]1[CH:34]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:35]1[CH:43]=[CH:42][C:38]([C:39]([NH:65][S:62]([CH3:61])(=[O:64])=[O:63])=[O:40])=[CH:37][C:36]=1[Cl:44])[CH2:31]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036044-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acidHCID 867036334-(Adamantan-2-yl(benzyloxy)methyl)-3-chlorobenzoic acid

Product 1

HCID 867036344-(adamantan-2-yl(benzyloxy)methyl)-3-chloro-N-(methylsulfonyl)benzamide

Procedure

Following the procedure as described in Example 299 Step 2 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acid with 4-(adamantan-2-yl(benzyloxy)methyl)-3-chlorobenzoic acid and to replace azetidine-1-sulfonamide with methanesulfonamide, the title compound was obtained as a colorless solid (0.312 g, 61%): 1H NMR (300 MHz, DMSO-d6) δ 12.24 (br s, 1H), 8.04 (d, J=1.7 Hz, 1H), 7.97 (d, J=7.9 Hz, 1H), 7.71 (d, J=8.1 Hz, 1H), 7.37-7.22 (m, 5H), 5.08 (d, J=9.9 Hz, 1H), 4.27 (d, J=11.8 Hz, 1H), 4.16 (d, J=11.8 Hz, 1H), 3.37 (s, 3H), 2.38-2.31 (m, 1H), 2.09-1.34 (m, 13H), 1.08-1.02 (m, 1H); MS (ES−) m/z 486.2, 488.2 (M−1).

Sources & evidence

ORD record
ord-aab1eee248c9443795be5c1a4a751152
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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