Hexanoic Acid → HCID 178442279, compound

HRID 1985654Notes

Reaction equation

[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:9][C:10]1[CH:11]=[C:12]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[O:24])[CH2:19][CH2:18]2)[CH:13]=[CH:14][C:15]=1[NH2:16]>>[CH2:2]([C:1]1[NH:16][C:15]2[CH:14]=[CH:13][C:12]([N:17]3[CH2:18][CH2:19][N:20]([C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])=[O:24])[CH2:21][CH2:22]3)=[CH:11][C:10]=2[N:9]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Reactant 2

HCID 8892Hexanoic Acid

HCID 66863203HCID 66863203, compound

Product 1

HCID 178442279HCID 178442279, compoundYield 57%

Procedure

Following the procedure as described in Example 3, making variations only as required to use n-hexanoic acid in place of butyric acid to react with [4-(3,4-diaminophenyl)piperazin-1-yl](2-trifluoromethylphenyl)methanone, the title compound was obtained as a yellow syrup in 57% yield (0.347 g). 1H NMR (300 MHz, CDCl3) δ 8.8 (br., s, 1H), 7.70 (d, J=7.7 Hz, 1H), 7.64-7.45 (m, 2H), 7.36 (d, J=8.7 Hz, 1H), 6.99 (s, 1H), 6.87 (dd, J=1.9, 8.7 Hz, 1H), 4.00-3.91 (m, 2H), 3.33 (t, J=4.8 Hz, 2H), 3.15 (t, J=5.1 Hz, 2H), 3.05-2.95 (m, 2H), 2.82 (t, J=7.7 Hz, 2H), 1.85-1.70 (m, 2H), 1.33-1.16 (m, 4H), 0.79 (t, J=7.0 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.5, 155.3, 147.4, 138.4, 134.5, 134.0, 132.3, 129.3, 127.2, 127.1, 126.8, 126.8, 126.7, 126.6, 125.4, 121.8, 115.4, 115.3, 114.9, 102.3, 51.3, 51.1, 47.3, 41.9, 31.4, 29.1, 27.9, 22.3, 13.9. MS (ES+) m/z 445.2 (M+1).

Sources & evidence

ORD record: ord-aba623538bbb4cc3a27ff7e4aa3ff137
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547698B2

Reaction notes

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