Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-5-bromo-2-fluoro-N-(methylsulfonyl)benzamide

HRID 1849747Notes

Reaction equation

HRID 1849747 reaction equation
C12(COC3C(I)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[C:24]12([CH2:34][O:35][C:36]3[C:44]([Br:45])=[CH:43][C:39]([C:40](O)=[O:41])=[C:38]([F:46])[CH:37]=3)[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2.N1(S(N)(=O)=O)CCC1.[CH3:55][S:56]([NH2:59])(=[O:58])=[O:57]>>[C:24]12([CH2:34][O:35][C:36]3[C:44]([Br:45])=[CH:43][C:39]([C:40]([NH:59][S:56]([CH3:55])(=[O:58])=[O:57])=[O:41])=[C:38]([F:46])[CH:37]=3)[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036044-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acidHCID 867036284-(Adamantan-1-ylmethoxy)-5-bromo-2-fluorobenzoic acid

Product 1

HCID 867036294-(adamantan-1-ylmethoxy)-5-bromo-2-fluoro-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-1-ylmethoxy)-5-bromo-2-fluorobenzoic acid and to replace azetidine-1-sulfonamide with methanesulfonamide, the title compound was obtained as a colorless solid (1.00 g, 49%): 1H NMR (300 MHz, DMSO-d6) δ 12.10 (br s, 1H), 7.90 (d, J=7.3 Hz, 1H), 7.17 (d, J=12.4 Hz, 1H), 3.71 (s, 2H), 3.35 (s, 3H), 1.98 (br s, 3H), 1.78-1.56 (m, 12H); MS (ES−) m/z 458.2, 460.1 (M−1).

Sources & evidence

ORD record
ord-dc3b0679f6cb41cc9102164a8e1eec81
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…