Thiopheneethanamine → 4-{3-Chloro-5-[(2-thiophen-2-yl-ethylamino)-methyl]-pyridin-2-yloxy}-benzamide

HRID 228349Notes

Reaction equation

HRID 228349 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.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][CH2:26][NH2:27]>>[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:27][CH2:26][CH2:25][C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 116521ThiopheneethanamineHCID 597301934-(3-Chloro-5-formyl-pyridin-2-yloxy)-benzamide

Product 1

HCID 597301294-{3-Chloro-5-[(2-thiophen-2-yl-ethylamino)-methyl]-pyridin-2-yloxy}-benzamideYield 36%

Procedure

Using a method similar to Example 460, using 4-(3-chloro-5-formyl-pyridin-2-yloxy)-benzamide (114 mg, 0.412 mmol) and 2-thiophen-2-yl-ethylamine (0.048 mL, 0.412 mmol) gives the title compound (57 mg, 36%). Mass spectrum (ion spray): m/z=387.9 (M+1); 1H NMR (DMSO-d6): 8.37 (bs, 1H), 8.21 (d, J=1.9 Hz, 1H), 7.99 (bs, 1H), 7.93 (d, J=8.7 Hz, 2H), 7.39 (dd, J=1.2 Hz, 5.0 Hz, 1H), 7.36 (bs, 1H), 7.21 (d, J=8.9 Hz, 2H), 6.99-6.94 (m, 2H), 4.16 (s, 2H), 3.26-3.11 (m, 4H).

Sources & evidence

ORD record
ord-7f02275551364060ad58a78569694cea
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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