Cyclopropanesulfonamide → HCID 86703602, compound

HRID 1849726Notes

Reaction equation

HRID 1849726 reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=CN=3)CC3CC(CC(C3)C1)C2.[C:25]12([CH2:35][O:36][C:37]3[C:45]([CH:46]4[CH2:48][C:47]4([F:50])[F:49])=[CH:44][C:40]([C:41](O)=[O:42])=[C:39]([F:51])[CH:38]=3)[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.COCCS(N)(=O)=O.[CH:60]1([S:63]([NH2:66])(=[O:65])=[O:64])[CH2:62][CH2:61]1>>[C:25]12([CH2:35][O:36][C:37]3[C:45]([CH:46]4[CH2:48][C:47]4([F:50])[F:49])=[CH:44][C:40]([C:41]([NH:66][S:63]([CH:60]4[CH2:62][CH2:61]4)(=[O:65])=[O:64])=[O:42])=[C:39]([F:51])[CH:38]=3)[CH2:32][CH:31]3[CH2:33][CH:27]([CH2:28][CH:29]([CH2:30]3)[CH2:34]1)[CH2:26]2

Participants

5

Reactant 4

HCID 15765418CyclopropanesulfonamideHCID 189515062-Methoxyethane-1-sulfonamideHCID 867029246-(Adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acidHCID 86703599HCID 86703599, compound

Product 1

HCID 86703602HCID 86703602, compoundYield 43%

Procedure

Following the procedure as described in Example 271 and making variations as required to replace 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acid with 4-(adamantan-1-ylmethoxy)-5-(2,2-difluorocyclopropyl)-2-fluorobenzoic acid and to replace 2-methoxyethanesulfonamide with cyclopropylsulfonamide. Purification by silica gel column chromatography (2:1 hexanes:ethyl acetate (+0.2% acetic acid v/v)) gave the title compound as a colorless solid (0.055 g, 43%): 1H NMR (300 MHz, DMSO-d6) δ 11.86 (br s, 1H), 7.44 (d, J=8.2 Hz, 1H), 7.00 (d, J=13.0 Hz, 1H), 3.70-3.56 (m, 2H), 3.10-2.99 (m, 1H), 2.84-2.71 (m, 1H), 2.04-1.85 (m, 5H), 1.76-1.55 (m, 12H), 1.14-1.02 (m, 4H); MS (ES+) m/z 484.1 (M+1).

Workup

  1. customPurification by silica gel column chromatography (2:1 hexanes

Sources & evidence

ORD record
ord-35fea53eb5e44a3eaab47fcac2248c81
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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