4-Morpholinesulfonamide → 4-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-3-(trifluoromethyl)benzamide

HRID 1427869Notes

Reaction equation

HRID 1427869 reaction equation
C12(COC3C(Cl)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[C:24]12([CH2:34][O:35][C:36]3[CH:44]=[CH:43][C:39]([C:40]([OH:42])=O)=[CH:38][C:37]=3[C:45]([F:48])([F:47])[F:46])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2.[N:49]1([S:55]([NH2:58])(=[O:57])=[O:56])[CH2:54][CH2:53]OC[CH2:50]1.N1(S(N)(=O)=O)CCC1>>[C:24]12([CH2:34][O:35][C:36]3[CH:44]=[CH:43][C:39]([C:40]([NH:58][S:55]([N:49]4[CH2:54][CH2:53][CH2:50]4)(=[O:57])=[O:56])=[O:42])=[CH:38][C:37]=3[C:45]([F:47])([F:48])[F:46])[CH2:25][CH:26]3[CH2:32][CH:30]([CH2:29][CH:28]([CH2:27]3)[CH2:33]1)[CH2:31]2

Participants

5

Reactant 4

HCID 2767394-MorpholinesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867028594-(Adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acidHCID 867028914-(Adamantan-1-ylmethoxy)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 867028924-(adamantan-1-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-3-(trifluoromethyl)benzamide

Procedure

Following the procedure as described in Example 98 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acid with 4-(adamantan-1-ylmethoxy)-3-(trifluoromethyl)benzoic acid and morpholine-4-sulfonamide with azetidine-1-sulfonamide, the title compound was obtained as a colorless solid (0.05 g, 22%): 1H NMR (300 MHz, DMSO-d6) 11.92 (s, 1H), 8.26-8.22 (m, 2H), 7.38-7.35 (m, 1H), 4.05 (t, J=7.7 Hz, 4H), 3.76 (s, 2H), 2.20-2.09 (m, 2H), 1.99 (br s, 3H), 1.75-1.63 (m, 12H); MS (ES−) m/z 471.3 (M−1); MS (ES+) m/z 473.2 (M+1).

Sources & evidence

ORD record
ord-02f72091b91244e191dda7a692305c0a
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

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