Ethanol → N-[6-(4-amino-3-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095849Notes

Reaction equation

HRID 2095849 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[N+:24]([O-])=O)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1.[Cl-].[NH4+].C(O)C.O1CCCC1>O>[NH2:24][C:23]1[CH:22]=[CH:21][C:4]([O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])[N:14]=3)[CH:11]=2)=[CH:3][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 58158527N-[6-(3-chloro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 58158556N-[6-(4-amino-3-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using N-[6-(3-chloro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (300 mg, 0.805 mmol), reduced iron (237 mg, 4.02 mmol), ammonium chloride (430 mg, 8.05 mmol), ethanol (2 mL), tetrahydrofuran (2 mL) and water (0.5 mL), and in the same manner as in Reference Example 105, the title compound (166 mg, 60%) was obtained as a white solid.

Sources & evidence

ORD record
ord-5454356e3bab4d22b2ee746866805a28
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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