2-Methoxyethane-1-sulfonamide → 4-(cyclopentylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

HRID 1849743Notes

Reaction equation

HRID 1849743 reaction equation
C12(COC3C(I)=CC(C(O)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[CH:24]1([CH2:29][O:30][C:31]2[C:39]([CH:40]3[CH2:42][CH2:41]3)=[CH:38][C:34]([C:35]([OH:37])=O)=[C:33]([F:43])[CH:32]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1.N1(S(N)(=O)=O)CCC1.[CH3:52][O:53][CH2:54][CH2:55][S:56]([NH2:59])(=[O:58])=[O:57]>>[CH:24]1([CH2:29][O:30][C:31]2[C:39]([CH:40]3[CH2:42][CH2:41]3)=[CH:38][C:34]([C:35]([NH:59][S:56]([CH2:55][CH2:54][O:53][CH3:52])(=[O:58])=[O:57])=[O:37])=[C:33]([F:43])[CH:32]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 4

HCID 189515062-Methoxyethane-1-sulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036044-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acidHCID 867036214-(Cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867036244-(cyclopentylmethoxy)-5-cyclopropyl-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide

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-(cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace azetidine-1-sulfonamide with 2-methoxyethanesulfonamide, the title compound was obtained as a colorless solid (0.039 g, 12%): 1H NMR (300 MHz, DMSO-d6) δ 11.88 (br s, 1H), 7.10 (d, J=8.3 Hz, 1H), 6.93 (d, J=13.0 Hz, 1H), 3.96 (d, J=6.8 Hz, 2H), 3.71 (s, 4H), 3.21 (s, 3H), 2.42-2.26 (m, 1H), 2.07-1.96 (m, 1H), 1.86-1.73 (m, 2H), 1.68-1.47 (m, 4H), 1.44-1.30 (m, 2H), 0.92-0.84 (m, 2H), 0.70-0.62 (m, 2H); 19F NMR (282 MHz, DMSO-d6) δ −113.0 (s, 1F); MS (ES−) m/z 398.2 (M−1).

Sources & evidence

ORD record
ord-a466f97d5c1746c1a986f3412e114ab8
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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