Stannous chloride dihydrate → N-(3-(6-amino-1H-imidazo[4,5-b]pyridin-2-yl)-4-chlorophenyl)furan-2-carboxamide

HRID 713691Notes

Reaction equation

HRID 713691 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[CH:4][C:3]=1[C:16]1[NH:17][C:18]2[C:19]([N:27]=1)=[N:20][CH:21]=[C:22]([N+:24]([O-])=O)[CH:23]=2.O.O.Cl[Sn]Cl>C(O)C>[NH2:24][C:22]1[CH:23]=[C:18]2[NH:17][C:16]([C:3]3[CH:4]=[C:5]([NH:8][C:9]([C:11]4[O:12][CH:13]=[CH:14][CH:15]=4)=[O:10])[CH:6]=[CH:7][C:2]=3[Cl:1])=[N:27][C:19]2=[N:20][CH:21]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 85471033HCID 85471033, compound

Product 1

HCID 78425811N-(3-(6-amino-1H-imidazo[4,5-b]pyridin-2-yl)-4-chlorophenyl)furan-2-carboxamideYield 54.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of N-(4-chloro-3-[6-nitro-1H-imidazo[4,5-b]pyridin-2-yl]phenyl)furan-2-carboxamide (3.9 g, 10.16 mmol, 1.00 equiv) in ethanol (50 mL) was added SnCl2.2H2O (3.4 g, 15.04 mmol, 1.48 equiv) and heated to reflux overnight. The reaction mixture was concentrated under vacuum and diluted with H2O. The pH value of the mixture was adjusted to 9 with sodium carbonate (sat.). The solids were collected by filtration and applied onto a silica gel column with ethyl acetate/PE (3/1) to give 1.95 g (54%) of N-(3-[6-amino-1H-imidazo[4,5-b]pyridin-2-yl]-4-chlorophenyl)furan-2-carboxamide as a yellow solid. 1H-NMR: (CD3OD, 400 MHz): 8.16 (d, J=2.4 Hz, 1H), 7.97-8.10 (m, 2H), 7.78 (d, J=0.8 Hz, 1H), 7.65 (d, J=20.0 Hz, 1H), 7.31-7.41 (m, 2H), 6.68 (dd, J=3.6, 2.0 Hz, 1H. MS (M+H)+=354.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additiondiluted with H2O
  5. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-525cdce119a64437ab6f8e7458c0ff57
Source dataset
uspto-grants-2015_11
Patent number
US09186361B2

Reaction notes

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