Cyclopropanesulfonamide → 4-(cyclopentylmethoxy)-5-cyclopropyl-N-(cyclopropylsulfonyl)-2-fluorobenzamide

HRID 1849741Notes

Reaction equation

HRID 1849741 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.[CH:52]1([S:55]([NH2:58])(=[O:57])=[O:56])[CH2:54][CH2:53]1>C(OCC)C>[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:58][S:55]([CH:52]3[CH2:54][CH2:53]3)(=[O:57])=[O:56])=[O:37])=[C:33]([F:43])[CH:32]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 15765418CyclopropanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036044-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acidHCID 867036214-(Cyclopentylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867036204-(cyclopentylmethoxy)-5-cyclopropyl-N-(cyclopropylsulfonyl)-2-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 cyclopropane-sulfonamide, the title compound was obtained as a colorless solid (0.039 g, 12%) after trituration in diethyl ether followed by trituration in methanol: 1H NMR (300 MHz, DMSO-d6) δ 11.81 (br s, 1H), 7.12 (d, J=8.3 Hz, 1H), 6.96 (d, J=13.1 Hz, 1H), 3.97 (d, J=6.8 Hz, 2H), 3.13-3.02 (m, 1H), 2.41-2.26 (m, 1H), 2.08-1.95 (m, 1H), 1.85-1.72 (m, 2H), 1.68-1.49 (m, 4H), 1.44-1.31 (m, 2H), 1.15-1.07 (m, 4H), 0.93-0.85 (m, 2H), 0.71-0.64 (m, 2H); MS (ES−) m/z 380.2 (M−1).

Sources & evidence

ORD record
ord-5b61d0994681487abf73b5dd059e2dff
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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