1-Naphthalenesulfonyl chloride → N-(6-(3-(Naphthalene-1-sulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162438Notes

Reaction equation

HRID 1162438 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([NH:14][C:15]3[CH:16]=[C:17]([C:21]4[CH:22]=[CH:23][C:24]5[N:25]([CH:27]=[C:28]([NH:30][C:31](=[O:33])[CH3:32])[N:29]=5)[N:26]=4)[CH:18]=[CH:19][CH:20]=3)(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3]N=1.N[C:35]1C=C(C2C=CC3N(C=C(NC(=O)C)N=3)N=2)C=CC=1.C1(S(Cl)(=O)=O)C2C(=CC=CC=2)C=CC=1>>[C:6]1([S:11]([NH:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:22]=[CH:23][C:24]4[N:25]([CH:27]=[C:28]([NH:30][C:31](=[O:33])[CH3:32])[N:29]=4)[N:26]=3)[CH:18]=[CH:19][CH:20]=2)(=[O:12])=[O:13])[C:5]2[C:10](=[CH:1][CH:35]=[CH:3][CH:4]=2)[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 665601-Naphthalenesulfonyl chlorideHCID 44124634N-(6-(3-(Isoquinoline-5-sulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamideHCID 57749413N-(6-(3-Aminophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Product 1

HCID 44124749N-(6-(3-(Naphthalene-1-sulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Procedure

Following the procedure for compound N-(6-(3-(isoquinoline-5-sulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (Example 6), N-(6-(3-aminophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (Example 5) (0.032 g, 0.12 mmol) was reacted with 1-naphthalenesulfonyl chloride (0.034 g, 0.15 mmol, Aldrich, St. Louis, Mo.) to afford the title compound as a white solid. MS (ESI positive ion) m/z: 458 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.92 (s, 1H), 10.91 (s, 1H), 8.77 (d, J=8.6 Hz, 1H), 8.30 (d, J=7.4 Hz, 1H), 8.21-8.24 (m, 2H), 8.07 (d, J=8.0 Hz, 1H), 8.02 (d, J=9.4 Hz, 1H), 7.74-7.78 (m, 1H), 7.62-7.70 (m, 3H), 7.58 (d, J=7.8 Hz, 1H), 7.53 (d, J=9.4 Hz, 1H), 7.32 (t, J=7.9 Hz, 1H), 7.16 (dd, J=8.0 Hz, 1.6 Hz, 1H), 2.11 (s, 3H).

Sources & evidence

ORD record
ord-c19ef89fefa94fac91e7cde3f8c5aba4
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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