Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-2-fluoro-5-(trans-2-(methoxymethyl)-cyclopropyl)-N-(methylsulfonyl)benzamide
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]([C@@H:45]4[CH2:47][C@H:46]4[CH2:48][O:49][CH3:50])=[CH:43][C:39]([C:40](O)=[O:41])=[C:38]([F:51])[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.[CH3:60][S:61]([NH2:64])(=[O:63])=[O:62]>>[C:24]12([CH2:34][O:35][C:36]3[C:44]([C@@H:45]4[CH2:47][C@H:46]4[CH2:48][O:49][CH3:50])=[CH:43][C:39]([C:40]([NH:64][S:61]([CH3:60])(=[O:63])=[O:62])=[O:41])=[C:38]([F:51])[CH:37]=3)[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2Participants
5
Reactant 4
Product 1
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)-2-fluoro-5-(trans-2-(methoxymethyl)cyclopropyl)benzoic acid and to replace azetidine-1-sulfonamide with methanesulfonamide, the title compound was obtained as a colorless solid (0.0678 g, quant.): 1H NMR (300 MHz, DMSO-d6) δ 11.89 (br s, 1H), 7.18 (d, J=8.3 Hz, 1H), 6.93 (d, J=13.1 Hz, 1H), 3.66 (d, J=9.4 Hz, 1H), 3.61 (d, J=9.5 Hz, 1H), 3.46-3.35 (m, 2H), 3.34 (s, 3H), 3.25 (s, 3H), 2.04-1.89 (m, 4H), 1.78-1.61 (m, 12H), 1.34-1.22 (m, 1H), 1.06-0.97 (m, 1H), 0.90-0.81 (m, 1H); MS (ES−) m/z 464.2 (M−1).
Sources & evidence
- ORD record
- ord-08f24091e5024bd19b53df06e8632778
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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