2-Chloro-6-methylbenzene-1-sulfonyl chloride → HCID 44125258, compound

HRID 1162472Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[N:17]=3)[N:14]=2)[CH:5]=[N:6][C:7]=1[Cl:8].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[Cl:8][C:7]1[N:6]=[CH:5][C:4]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[N:17]=3)[N:14]=2)=[CH:3][C:2]=1[NH:1][S:30]([C:24]1[C:25]([CH3:29])=[CH:26][CH:27]=[CH:28][C:23]=1[Cl:22])(=[O:31])=[O:32]

Participants

Conditions

Temperature: 25 °C

Procedure

To a 50 mL, round-bottomed flask was added N-(6-(5-amino-6-chloropyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide from Step 2 (30 mg, 99 μmol), 2-chloro-6-methylbenzenesulfonyl chloride (149 μl, 661 μmol, Alfa Aesar, Ward Hill, Mass.), and pyridine (5 mL). The reaction mixture was stirred at 25° C. for 15 h and concentrated in high vacuum. Purification by silica gel chromatography (5 to 20% MeOH/CH2Cl2 provided N-(6-(6-chloro-5-(2-chloro-6-methylphenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (20 mg, 41% yield) as an off-white solid. MS (ESI positive ion) m/z: 491 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.13 (s, 3H), 2.59 (s, 3H), 7.37 (d, J=7.03 Hz, 1H), 7.50 (q, J=7.53 Hz, 2H), 7.83 (d, J=9.54 Hz, 1H), 8.13 (d, J=9.03 Hz, 1H), 8.31 (s, 1H), 8.38 (s, 1H), 8.91 (s, 1H), 10.71 (s, 1H), 10.99 (s, 1H).

Workup

concentrationconcentrated in high vacuum
customPurification by silica gel chromatography (5 to 20% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-bd2ade2b866b4596a27545f8cab4033b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820665B2

Reaction notes

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