Dichloromethane → 1-(4-Amino-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone

HRID 1868328

Reaction equation

Cl[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[C:5]([C:17](=[O:19])[CH3:18])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].COC1C=CC(C[NH2:33])=CC=1.ClCCl>CN(C=O)C.CO>[NH2:33][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[C:5]([C:17](=[O:19])[CH3:18])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of 1-(4-chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone 97 (61 mg, 0.21 mmol) and potassium carbonate (174 mg, 1.26 mmol) in DMF (1.8 mL) was added 4-methoxybenzylamine (85 μl, 0.64 mmol). The resultant mixture was heated at 50° C. for 6.75 h. After this time, 20 mL of a 1:1 mixture of dichloromethane and methanol was added and the resultant slurry was filtered. The filtrate was concentrated and the residue was dissolved in trifluoroacetic acid (7 mL). The resultant mixture was heated at 55° C. for 2.75 h. After this time, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluent: dichloromethane:MeOH:Et3N, 98.5:1.5:0.5) to give 98.

Workup

additionwas added
filtrationthe resultant slurry was filtered
concentrationThe filtrate was concentrated
dissolutionthe residue was dissolved in trifluoroacetic acid (7 mL)
concentrationAfter this time, the reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography (eluent: dichloromethane:MeOH:Et3N, 98.5:1.5:0.5)

Sources & evidence

ORD record: ord-d145112c00254d549092af405f18581f
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635695B2

Linked notes

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