Hydrochloric Acid → 2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine

HRID 1821390Notes

Reaction equation

HRID 1821390 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([N+:24]([O-])=O)=[C:11]([CH:13]=[CH:14][C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][N:16]=3)[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Sn].Cl>C(O)C>[NH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH:14]=[CH:13][C:11]2[CH:12]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[CH:8]=[CH:9][C:10]=2[NH2:24])=[N:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 69002915HCID 69002915, compound

Product 1

HCID 690043002-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to Example 1, (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.12 g, 0.25 mmol) was dissolved in methanol (6.0 mL) and crude 3-{2-[5-(morpholin-4-yl)-2-nitrophenyl]vinyl}-1H-indazole was obtained from 5-morpholino-2-nitrobenzaldehyde (65 mg, 0.25 mmol) and potassium carbonate (0.10 g, 0.75 mmol). In a similar manner to Example 2, crude 3-{2-[5-(morpholin-4-yl)-2-nitrophenyl]vinyl}-1H-indazole (0.80 g, 2.3 mmol) was dissolved in ethanol (25 mL) and the solution was added with tin (0.82 g, 6.9 mmol) and concentrated hydrochloric acid (4.0 mL) and heated from room temperature to 40° C. to obtain 2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine. Further, in a similar manner to Example 29, 2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine (0.45 g, 1.4 mmol) was dissolved in THF (10 mL) and the solution was added with triethylamine (0.61 ml, 4.2 mmol) and 3-methylthiophenecarbonylchloride (0.20 g, 1.4 mmol) and stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure to obtain free base of Compound 225. Further, said free base was treated by 4 mol/L hydrogen chloride-methanol solution (1.0 mL) to obtain Compound 225 (0.40 g, 55%).

Workup

  1. temperatureheated from room temperature to 40° C.

Sources & evidence

ORD record
ord-8cddacce623e41a780e0a8ab3a1e252c
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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