5648-88-4 → 6-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]imidazo[1,2-B]pyridazine-2-carboxylic acid (3-cyclopropylpropyl)amide

HRID 1985644Notes

Reaction equation

HRID 1985644 reaction equation
[CH:1]1([CH2:4][CH2:5][CH2:6][NH2:7])[CH2:3][CH2:2]1.C([O:10][C:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:39])[C:28]4[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=4[C:35]([F:38])([F:37])[F:36])[CH2:23][CH2:22]3)=[N:17][N:16]2[CH:40]=1)=O)C>>[CH:1]1([CH2:4][CH2:5][CH2:6][NH:7][C:11]([C:13]2[N:14]=[C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([C:27](=[O:39])[C:28]5[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=5[C:35]([F:36])([F:38])[F:37])[CH2:23][CH2:22]4)=[N:17][N:16]3[CH:40]=2)=[O:10])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 204265045648-88-4HCID 668634596-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]imidazo[1,2-B]pyridazine-2-carboxylic acid ethyl ester

Product 1

HCID 116779956-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]imidazo[1,2-B]pyridazine-2-carboxylic acid (3-cyclopropylpropyl)amideYield 46%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 3-(cyclopropyl)propylamine in place of isoamylamine to react with 6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]imidazo[1,2-b]pyridazine-2-carboxylic acid ethyl ester, the title compound was obtained as a white solid in 46% yield (0.079 g). 1H NMR (300 MHz, CDCl3) δ 8.15 (d, J=0.6 Hz, 1H), 7.76-7.71 (m, 1H), 7.68 (d, J=9.9 Hz, 1H), 7.30-7.18 (m, 2H), 7.09-7.03 (m, 1H), 6.87 (d, J=9.9 Hz, 1H), 4.04-3.93 (m, 1H), 3.91-3.8 (m, 1H), 3.64-3.54 (m, 2H), 3.51-3.4 (m, 4H), 3.37-3.29 (m, 2H), 1.77-1.65 (m, 2H), 1.32-1.23 (m, 2H), 0.71-0.61 (m 1H), 0.42-0.37 (m, 2H), 0.08-0.03 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 165.9, 162.5, 162.3, 154.7, 138.4, 136.9, 135.6, 129.61, 129.6, 129.5, 126.4, 126.36, 125.0, 123.3, 122.9, 121.4, 118.1, 116.7, 116.5, 114.7, 114.57, 111.8, 46.2, 45.5, 41.2, 38.8, 31.9, 29.7, 10.4, 4.4. MS (ES+) m/z 519 (M+1).

Sources & evidence

ORD record
ord-bbf61ef2152745a481718147430919a0
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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