Methanesulfonyl chloride → 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((tetrahydrofuran-3-yl)sulfonyl)benzamide

HRID 1849623Notes

Reaction equation

HRID 1849623 reaction equation
C12(COC3C=CC(C(N)=O)=CC=3C3C(OC)=NC=CC=3)CC3CC(CC(C3)C1)C2.[C:30]12([CH2:40][O:41][C:42]3[C:50]([CH:51]4[CH2:53][CH2:52]4)=[CH:49][C:45]([C:46]([NH2:48])=[O:47])=[C:44]([F:54])[CH:43]=3)[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2.CS(Cl)(=O)=O.[O:60]1[CH2:64][CH2:63][CH:62]([S:65](Cl)(=[O:67])=[O:66])[CH2:61]1>>[C:30]12([CH2:40][O:41][C:42]3[C:50]([CH:51]4[CH2:52][CH2:53]4)=[CH:49][C:45]([C:46]([NH:48][S:65]([CH:62]4[CH2:63][CH2:64][O:60][CH2:61]4)(=[O:67])=[O:66])=[O:47])=[C:44]([F:54])[CH:43]=3)[CH2:37][CH:36]3[CH2:38][CH:32]([CH2:33][CH:34]([CH2:35]3)[CH2:39]1)[CH2:31]2

Participants

5

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 49762850Oxolane-3-sulfonyl chlorideHCID 867028454-(Adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamideHCID 867034794-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzamide

Product 1

HCID 867034784-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluoro-N-((tetrahydrofuran-3-yl)sulfonyl)benzamide

Procedure

Following the procedure as described in Example 38 step 4 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamide with 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzamide and to replace methanesulfonyl chloride with tetrahydrofuran-3-sulfonyl chloride, the title compound was obtained as a colorless solid (0.14 g, 28%): 1H NMR (300 MHz, CDCl3) δ8.72-8.60 (m, 1H), 7.60-7.53 (m, 1H), 6.63-6.53 (m, 1H), 4.62-4.48 (m, 1H), 4.33-4.23 (m, 1H), 4.16-3.82 (m, 3H), 3.56 (s, 2H), 2.58-2.44 (m, 1H), 2.42-2.26 (m, 1H), 2.10-1.99 (m, 4H), 1.84-1.66 (m, 12H), 1.00-0.89 (m, 2H), 0.70-0.61 (m, 2H); MS (ES+) m/z 478.1 (M+1).

Sources & evidence

ORD record
ord-aa97633ccec246218accd0e7573d2043
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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