1-Azetidinesulfonamide → 4-(cyclopentylmethoxy)-5-cyclopropyl-2-fluoro-N-((3-methoxyazetidin-1-yl)sulfonyl)benzamide

HRID 1849742Notes

Reaction equation

HRID 1849742 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][CH:54]1[CH2:57][N:56]([S:58]([NH2:61])(=[O:60])=[O:59])[CH2:55]1>CO>[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:61][S:58]([N:56]3[CH2:57][CH:54]([O:53][CH3:52])[CH2:55]3)(=[O:60])=[O:59])=[O:37])=[C:33]([F:43])[CH:32]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 450805661-AzetidinesulfonamideHCID 867036044-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acidHCID 867036214-(Cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036233-Methoxyazetidine-1-sulfonamide

Product 1

HCID 867036224-(cyclopentylmethoxy)-5-cyclopropyl-2-fluoro-N-((3-methoxyazetidin-1-yl)sulfonyl)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 azetidine-1-sulfonamide with 3-methoxyazetidine-1-sulfonamide, the title compound was obtained as a colorless solid (0.04 g, 11%) after trituration in methanol: 1H NMR (300 MHz, DMSO-d6) δ 11.70 (br s, 1H), 7.12 (d, J=8.3 Hz, 1H), 6.96 (d, J=13.0 Hz, 1H), 4.24-4.11 (m, 3H), 3.99-3.91 (m, 4H), 3.17 (s, 3H), 2.43-2.26 (m, 1H), 2.08-1.95 (m, 1H), 1.86-1.73 (m, 2H), 1.69-1.50 (m, 4H), 1.45-1.31 (m, 2H), 0.93-0.85 (m, 2H), 0.71-0.64 (m, 2H); MS (ES−) m/z 425.2 (M−1).

Sources & evidence

ORD record
ord-303f592773a7432ca5bcc03c965310f7
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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