2-Methoxyethane-1-sulfonamide → HCID 86703603, compound

HRID 1849727Notes

Reaction equation

HRID 1849727 reaction equation
C12(COC3C(C4CC4)=[CH:20][C:16](C(O)=O)=[CH:15][N:14]=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]([OH:43])=O)=[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.COCC[S:56]([NH2:59])(=[O:58])=[O:57]>>[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:59][S:56]([N:14]4[CH2:15][CH2:16][CH2:20]4)(=[O:58])=[O:57])=[O:43])=[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

4

Reactant 3

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

Product 1

HCID 86703603HCID 86703603, compoundYield 31%

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 azetidine 1-sulfamide. 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 (0.040 g, 31%): 1H NMR (300 MHz, DMSO-d6) δ 11.65 (br s, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.00 (d, J=12.9 Hz, 1H), 4.01 (t, J=7.7 Hz, 4H), 3.68-3.57 (m, 2H), 2.84-2.71 (m, 1H), 2.20-2.06 (m, 2H), 2.06-1.88 (m, 5H), 1.75-1.54 (m, 12H); MS (ES+) m/z 499.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-3d3e68fc6987403db9e1b6d788348f02
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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