4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide → HCID 86703525, compound

HRID 1849661Notes

Reaction equation

HRID 1849661 reaction equation
[CH:1]12[CH2:10]C3CC(CC(C3)[CH:2]1OCC1C(Cl)=CC(C(NS(C)(=O)=O)=O)=C(F)C=1)C2.Cl[C:29]1[C:30]([O:43][CH2:44][C:45]2([F:55])[CH:52]3[CH2:53][CH:48]4[CH2:49][CH:50]([CH2:54][CH:46]2[CH2:47]4)[CH2:51]3)=[CH:31][C:32]([F:42])=[C:33]([CH:41]=1)[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[O:35]>>[CH:10]1([C:29]2[C:30]([O:43][CH2:44][C:45]3([F:55])[CH:52]4[CH2:51][CH:50]5[CH2:49][CH:48]([CH2:47][CH:46]3[CH2:54]5)[CH2:53]4)=[CH:31][C:32]([F:42])=[C:33]([CH:41]=2)[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[O:35])[CH2:1][CH2:2]1

Participants

3

Reactant 2

HCID 867028574-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamideHCID 86703526HCID 86703526, compound

Product 1

HCID 86703525HCID 86703525, compound

Procedure

Following the procedure as described in Example 49 and making variations as required to replace 4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide with 5-chloro-2-fluoro-4-((2-fluoroadamantan-2-yl)methoxy)-N-(methylsulfonyl)benzamide, the title compound was obtained as a colorless solid (0.24 g, 74%): 1H NMR (300 MHz, CDCl3) δ8.77-8.65 (m, 1H), 7.63-7.56 (m, 1H), 6.68-6.58 (m, 1H), 4.30 (d, J=24.85 Hz, 2H), 3.42 (s, 3H), 2.34-2.16 (m, 4H), 2.14-2.01 (m, 1H), 1.97-1.85 (m, 4H), 1.84-1.72 (m, 4H), 1.72-1.62 (m, 2H), 1.00-0.90 (m, 2H), 0.70-0.61 (m, 2H); MS (ES−) m/z 438.1 (M−1).

Sources & evidence

ORD record
ord-0947f7b4cd3544fe8599d093deb84f59
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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