1-Bromohexan-2-one → HCID 11676354, compound

HRID 1985652Notes

Reaction equation

HRID 1985652 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH3:7].[NH2:9][C:10]1[N:15]=[N:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:32])[F:31])=[O:23])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1>>[CH2:4]([C:3]1[N:9]=[C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:17][CH2:18][N:19]([C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])=[O:23])[CH2:20][CH2:21]3)=[N:14][N:15]2[CH:2]=1)[CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 2

HCID 124317331-Bromohexan-2-oneHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 11676354HCID 11676354, compoundYield 42%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 1-bromohexan-2-one in place of 1-bromobutan-2-one to react with [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone, the title compound was obtained as a white solid in 42% yield. 1H NMR (300 MHz, CDCl3) δ 7.72-7.48 (m, 4H), 7.43 (s, 1H), 7.35-7.32 (m, 1H), 6.71 (d, J=9.9 Hz, 1H), 4.02-3.83 (m, 2H), 3.53 (m, 2H), 3.37-3.3 (m, 4H), 2.74-2.69 (m, 2H), 1.76-1.61 (m, 2H), 1.48-1.3 (m, 2H), 0.91 (t, J=7.2 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.4, 154.3, 146.8, 135.7, 134.4, 132.3, 129.4, 127.0, 126.8, 126.76, 126.7, 126.6, 126.2, 125.4, 125.3, 121.8, 113.6, 109.3, 46.5, 46.3, 46.2, 41.1, 31.5, 28.8, 22.4, 13.9. MS (ES+) m/z 432.3 (M+1).

Sources & evidence

ORD record
ord-bac011c9a635494d8821ad1a78015445
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

Loading…