Methanesulfonamide → 4-(adamantan-2-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)-sulfonyl)benzamide

HRID 1849647Notes

Reaction equation

HRID 1849647 reaction equation
C1(C2C(OCC3(C(F)(F)F)CCCCC3)=CC(F)=C(C=2)C(O)=O)CC1.[CH:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH:27]1[CH2:36][O:37][C:38]1[C:46]([CH:47]3[CH2:49][CH2:48]3)=[CH:45][C:41]([C:42](O)=[O:43])=[C:40]([F:50])[CH:39]=1)[CH2:33]2.CS(N)(=O)=O.[CH3:56][O:57][CH2:58][CH2:59][S:60]([NH2:63])(=[O:62])=[O:61]>>[CH:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH:27]1[CH2:36][O:37][C:38]1[C:46]([CH:47]3[CH2:48][CH2:49]3)=[CH:45][C:41]([C:42]([NH:63][S:60]([CH2:59][CH2:58][O:57][CH3:56])(=[O:62])=[O:61])=[O:43])=[C:40]([F:50])[CH:39]=1)[CH2:33]2

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 189515062-Methoxyethane-1-sulfonamideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867035094-(Adamantan-2-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867035104-(adamantan-2-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)-sulfonyl)benzamide

Procedure

Following the procedure as described in Example 158 step 5, and making variations as required to replace 5-cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)-benzoic acid with 4-(adamantan-2-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace methanesulfonamide with 2-methoxyethanesulfonamide, the title compound was obtained (0.16 g, 40%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.73-8.59 (m, 1H), 7.60-7.48 (m, 1H), 6.69-6.56 (m, 1H), 4.15-4.06 (m, 2H), 3.90-3.75 (m, 4H), 3.31 (s, 3H), 2.35-2.24 (m, 1H), 2.10-1.73 (m, 13H), 1.69-1.59 (m, 2H), 0.98-0.87 (m, 2H), 0.68-0.60 (m, 2H); MS (ES−) m/z 464.3 (M−1).

Sources & evidence

ORD record
ord-4d8210ca86bd4d2db45d6eaf807c26b5
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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