Hydrochloric Acid → HCID 68999162, compound

HRID 1821397Notes

Reaction equation

HRID 1821397 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[C:14]([O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH:15]=[CH:16][C:17]=2[N+:18]([O-])=O)=[N:2]1.[Sn].Cl>C(O)C>[CH2:27]([N:24]([CH2:25][CH3:26])[CH2:23][CH2:22][O:21][C:14]1[CH:15]=[CH:16][C:17]([NH2:18])=[C:12](/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)[CH:13]=1)[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 68999488HCID 68999488, compound

Product 1

HCID 68999162HCID 68999162, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude (E)-N-(2-{3-[2-(1H-indazol-3-yl)vinyl]-4-nitrophenyloxy}ethyl)diethylamine (2.0 g, 5.2 mmol) obtained in Step 1 was dissolved in ethanol (20 mL) and the solution was treated by tin (1.9 g, 16 mmol) and concentrated hydrochloric acid (1.0 mL) at room temperature in a similar manner to Example 2, to obtain (E)-{4-[2-(diethylamino)ethoxy]-2-[2-(1H-indazol-3-yl)vinyl]phenyl}amine. In a similar manner to Example 29, (E)-{4-[2-(diethylamino)ethoxy]-2-[2-(1H-indazol-3-yl)vinyl]phenyl}amine (0.49 g, 1.4 mmol) was dissolved in THF (15 mL) and the solution was added with triethylamine (0.58 ml, 4.2 mmol) and 3-methylthiophenecarbonyl chloride (0.23 g, 1.4 mmol), followed by stirring at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was triturated in ethyl acetate to obtain Compound 237 (0.42 g, 63%).

Sources & evidence

ORD record
ord-98d43f2224ff42d0a8d9dfec2074c55e
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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