1-Azetidinesulfonamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-((3-hydroxyadamantan-1-yl)methoxy)benzamide

HRID 1849673Notes

Reaction equation

HRID 1849673 reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[CH:26]1([C:29]2[C:30]([O:39][CH2:40][C:41]34[CH2:50][CH:45]5[CH2:46][CH:47]([CH2:49][C:43]([OH:51])([CH2:44]5)[CH2:42]3)[CH2:48]4)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34](O)=[O:35])[CH2:28][CH2:27]1.C([CH:54]1[CH2:57][N:56]([S:58]([NH2:61])(=[O:60])=[O:59])[CH2:55]1)#N.N1(S(N)(=O)=O)CCC1>>[N:56]1([S:58]([NH:61][C:34](=[O:35])[C:33]2[CH:37]=[C:29]([CH:26]3[CH2:28][CH2:27]3)[C:30]([O:39][CH2:40][C:41]34[CH2:50][CH:45]5[CH2:46][CH:47]([CH2:49][C:43]([OH:51])([CH2:44]5)[CH2:42]3)[CH2:48]4)=[CH:31][C:32]=2[F:38])(=[O:59])=[O:60])[CH2:55][CH2:54][CH2:57]1

Participants

5

Reactant 4

HCID 450805661-AzetidinesulfonamideHCID 867028614-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867035383-Cyanoazetidine-1-sulfonamideHCID 867035425-Cyclopropyl-2-fluoro-4-((3-hydroxyadamantan-1-yl)methoxy)benzoic acid

Product 1

HCID 86703541N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-((3-hydroxyadamantan-1-yl)methoxy)benzamide

Procedure

Following the procedure as described in Example 230 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-cyclopropyl-2-fluoro-4-((3-hydroxyadamantan-1-yl)methoxy)benzoic acid and to replace 3-cyanoazetidine-1-sulfonamide with azetidine-1-sulfonamide, the title compound was obtained as colorless solid (0.08 g, 65%): 1H NMR (300 MHz, DMSO-d6) δ 11.60 (s, 1H), 7.15 (d, J=8.3 Hz, 1H), 6.94 (d, J=12.9 Hz, 1H), 4.47 (s, 1H), 4.04 (t, J=7.7 Hz, 4H), 3.70 (s, 2H), 2.21-2.11 (m, 4H), 2.07-1.98 (m, 1H), 1.58-1.53 (m, 12H), 0.95-0.88 (m, 2H), 0.71-0.66 (m, 2H); MS (ES+) m/z 479.1 (M+1); MS (ES−) m/z 477.2 (M−1).

Sources & evidence

ORD record
ord-15acda5d70f3459b81b076911b4ca243
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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