Sulfamide → 4-[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-piperidine-1-sulfonic acid amide

HRID 1592599Notes

Reaction equation

[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[S:24](N)([NH2:27])(=[O:26])=[O:25]>O1CCOCC1>[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:10]2[CH2:15][CH2:14][N:13]([S:24]([NH2:27])(=[O:26])=[O:25])[CH2:12][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of COMPOUND 249 (0.1882 g, 0.61 mmol) in 1,4-dioxane (25 mL) was added sulfamide (0.5826 g, 6.06 mmol), and stirred at 100° C. for 4 hours. The mixture was concentrated and water (20 mL) was added and extracted with CH2Cl2 (2×75 mL). The combined organic extracts were washed with water (2×30 mL), dried (Na2SO4), filtered and concentrated. Purification of the crude material by column chromatography on silica gel (33:1:1 CH2Cl2-MeOH—NH4OH) provided 0.1461 g (59%) of COMPOUND 342 as a white solid. 1H NMR (CDCl3) δ 1.80-1.88 (m, 2H), 1.95-2.00 (m, 2H), 2.08 (s, 6H), 2.48-2.58 (m, 3H), 3.76-3.82 (m, 6H), 4.76 (s, 2H), 7.06-7.11 (m, 2H), 7.37 (d, 2H, J=7.2 Hz), 8.33 (d, 2H, J=3.0 Hz).

Workup

concentrationThe mixture was concentrated
additionwater (20 mL) was added
extractionextracted with CH2Cl2 (2×75 mL)
washThe combined organic extracts were washed with water (2×30 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customPurification of the crude material by column chromatography on silica gel (33:1:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record: ord-57205b4c1abe4ccc948908c7751adab3
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291631B2

Reaction notes

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