Butylamine → HCID 11569094, compound

HRID 1985646Notes

Reaction equation

[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C([O:8][C:9]([C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:36])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]([F:35])([F:34])[F:33])[CH2:21][CH2:20]3)=[N:15][N:14]2[CH:37]=1)=O)C>>[CH2:1]([NH:5][C:9]([C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:20][CH2:21][N:22]([C:25](=[O:36])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]([F:33])([F:35])[F:34])[CH2:23][CH2:24]3)=[N:15][N:14]2[CH:37]=1)=[O:8])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 8007Butylamine

HCID 66863489HCID 66863489, compound

Product 1

HCID 11569094HCID 11569094, compoundYield 72%

Procedure

Following the procedure as described in Example 1, making variations only as required to use n-butylamine in place of isoamylamine to react with 6-[4-(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 72% yield (0.077 g). m.p. 187-189° C. 1H NMR (300 MHz, CDCl3) δ 8.1 (s, 1H), 7.75-7.66 (m, 2H), 7.65-7.5 (m, 2H), 7.48-7.38 (m, 1H), 7.37-7.3 (m, 1H), 6.92 (d, J=9.6 Hz, 1H), 4.05-3.94 (m, 1H), 3.93-3.82 (m, 1H), 3.69-3.54 (m, 2H), 3.5-3.38 (m, 4H), 3.35-3.28 (m, 2H), 1.65-1.53 (m 2H), 1.47-1.33 (m, 2H), 0.92 (t, J=7.5 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.5, 161.9, 154.9, 137.7, 135.3, 134.2, 132.4, 129.5, 127.2, 126.8, 126.7, 126.2, 125.4, 121.8, 118.3, 112.3, 46.2, 46.1, 45.6, 41.1, 38.9, 31.7, 20.1, 13.8. MS (ES+) m/z 475.2 (M+1).

Sources & evidence

ORD record: ord-367f8b040fcc42608d354ee505f1eeeb
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547698B2

Reaction notes

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