2-Chloro-4-fluorobenzoyl chloride → HCID 69066341, compound

HRID 1822020Notes

Reaction equation

HRID 1822020 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:12]([N:14]1[CH2:19][CH2:18][CH:17]([O:20][C:21]2[CH:22]=[C:23]([NH2:27])[CH:24]=[CH:25][CH:26]=2)[CH2:16][CH2:15]1)[CH3:13]>>[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH:17]2[CH2:18][CH2:19][N:14]([CH2:12][CH3:13])[CH2:15][CH2:16]2)[CH:22]=1)=[O:5]

Participants

3

Reactant 2

HCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 450953783-[(1-Ethylpiperidin-4-yl)oxy]aniline

Product 1

HCID 69066341HCID 69066341, compound

Procedure

Using a method similar to Example 5, using 2-chloro-4-fluoro-benzoyl chloride (0.054 mL, 0.420 mmol) and 3-(1-ethyl-piperidin-4-yloxy)-phenylamine (preparation 29) gives the title compound as the free base (131 mg, 91%). Following a method similar to Example 2 gives the title compound as the hydrochloride salt (130 mg, white solid). Mp: 91° C.; mass spectrum (free base, ion spray): m/z=377.2 (M+1); 1H NMR (free base, CDCl3): 8.14 (bs, N—H), 7.68 (dd, J=6.1 Hz, 8.7 Hz, 1H), 7.40 (bs, 1H), 7.21 (t, J=8.1 Hz, 1H), 7.14 (dd, J=2.5 Hz, 8.3 Hz, 1H), 7.06-7.01 (m, 2H), 6.70 (dd, J=2.4 Hz, 8.3 Hz, 1H), 4.38-4.31 (m, 1H), 2.75-2.67 (bm, 2H), 2.41 (q, J=7.1 Hz, 2H), 2.33-2.24 (bm, 2H), 2.04-1.97 (bm, 2H), 1.87-1.78 (bm, 2H), 1.08 (t, J=7.4 Hz, 3H); Analysis calculated for C20H23Cl2FN2O2.0.25H2O: C, 57.49; H, 5.67; N, 6.70. Found C, 57.45; H, 5.31; N, 6.59.

Sources & evidence

ORD record
ord-15ebcf25d6e644d8b99693953a5b48bb
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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