Dimethylformamide → HCID 86701922, compound

HRID 715748Notes

Reaction equation

HRID 715748 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=12.C(N(C(C)C)C(C)C)C.CN(C)C=O.[N:25]([C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[C:26]=[O:27]>O1CCCC1.O>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([NH:10][C:26]([NH:25][C:28]3[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=3)=[O:27])[CH:7]=[CH:6][C:5]=12

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 66012Benzene, 1-isocyanato-4-nitro-HCID 81531DiisopropylethylamineHCID 11344042imidazo[1,2-a]pyridin-6-amine

Product 1

HCID 86701922HCID 86701922, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of imidazo[1,2-a]pyridin-6-amine (1 g, 7.21 mmol), N-ethyl-N-isopropylpropan-2-amine (2.51 ml, 14.42 mmol) and dimethylformamide (21.85 ml) was treated with a solution of 1-isocyanato-4-nitrobenzene (1.313 g, 8.00 mmol) in tetrahydrofuran (10.92 ml) which was added dropwise via syringe over 5 minutes. The reaction mixture was allowed to stir at room temperature for 6 hours, and water was added. The suspension was filtered with water washes to give the title compound after vacuum drying.

Workup

  1. additionwas added dropwise via syringe over 5 minutes
  2. filtrationThe suspension was filtered with water

Sources & evidence

ORD record
ord-97e85b35e0d74d3fa6aeb4067df1059b
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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