Sodium Carbonate → HCID 85471033, compound

HRID 713690Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([NH2:11])[C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl:12][C:13]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)=[O:24])=[CH:18][C:14]=1[C:15](O)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:12][C:13]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)=[O:24])=[CH:18][C:14]=1[C:15]1[NH:11][C:6]2[C:7]([N:10]=1)=[N:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2

Participants

Reactant 3

HCID 10340Sodium Carbonate

HCID 1252891HCID 1252891, compound

HCID 34801515-Nitropyridine-2,3-diamine

Product 1

HCID 85471033HCID 85471033, compoundYield 26.1%

Conditions

Temperature: 130 °C

Procedure

A mixture of 5-nitropyridine-2,3-diamine (1-2) (6 g, 38.93 mmol, 1.00 equiv) and 2-chloro-5-(furan-2-amido)benzoic acid (I-3) (10.4 g, 39.15 mmol, 1.00 equiv) in PPA (100 mL) was stirred overnight at 130° C. The reaction was then poured into water/ice and the pH value of the mixture was adjusted to 9 with sodium carbonate. The solids were collected by filtration and applied onto a silica gel column with ethyl acetate/petroleum ether (31) to give 3.9 g (26%) of N-(4-chloro-3-[6-nitro-1H-imidazo[4,5-b]pyridin-2-yl]phenyl)furan-2-carboxamide (I-3) as a light yellow solid.

Workup

filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-2e06db2390894bc588a0d60199f731bb
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186361B2

Reaction notes

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