3-Chlorophenethylamine → 4-(3-Chloro-5-{[2-(3-chloro-phenyl)-ethylamino]-methyl}-pyridin-2-yloxy)-benzamide

HRID 130898Notes

Reaction equation

HRID 130898 reaction equation
[Cl:1][C:2]1[C:3]([O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=2)=[N:4][CH:5]=[C:6]([CH:8]=O)[CH:7]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][NH2:29])[CH:24]=[CH:25][CH:26]=1>>[Cl:1][C:2]1[C:3]([O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=2)=[N:4][CH:5]=[C:6]([CH2:8][NH:29][CH2:28][CH2:27][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[CH:22]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 1393813-ChlorophenethylamineHCID 597301934-(3-Chloro-5-formyl-pyridin-2-yloxy)-benzamide

Product 1

HCID 597300394-(3-Chloro-5-{[2-(3-chloro-phenyl)-ethylamino]-methyl}-pyridin-2-yloxy)-benzamideYield 37.5%

Procedure

Using a method similar to Example 462, using 4-(3-chloro-5-formyl-pyridin-2-yloxy)-benzamide (101 mg, 0.365 mmol) and 2-(3-chloro-phenyl)-ethylamine (0.056 mL, 0.402 mmol) gives the title compound (57 mg, 36%). Mass spectrum (ion spray): m/z=415.9 (M+1); 1H NMR (CDCl3): 7.93 (d, J=1.7 Hz, 1H), 7.86 (d, J=8.7 Hz, 2H), 7.77 (d, J=1.7 Hz, 1H), 7.22-7.17 (m, 4H), 7.07 (d, J=7.0 Hz, 1H), 6.12 (bs, 2H), 3.74 (s, 2H), 2.87 (t, J=6.8 Hz, 2H), 2.78 (t, J=6.8 Hz, 2H), 1.42 (bs, 1H).

Sources & evidence

ORD record
ord-2eb3c0fc5ba849ce9a934527b5916efb
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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