Water → 2-(Imidazo[1,2-a]pyrazin-3-yl)-4-iodofuro[2,3-c]pyridin-7-amine

HRID 389566Notes

Reaction equation

HRID 389566 reaction equation
[N:1]1[CH:2]=[C:3]([C:10]2[O:19][C:13]3=[C:14]([NH2:18])[N:15]=[CH:16][CH:17]=[C:12]3[CH:11]=2)[N:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=12.C1C(=O)N([I:27])C(=O)C1.O>CN(C=O)C>[N:1]1[CH:2]=[C:3]([C:10]2[O:19][C:13]3=[C:14]([NH2:18])[N:15]=[CH:16][C:17]([I:27])=[C:12]3[CH:11]=2)[N:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 667602142-(Imidazo[1,2-a]pyrazin-3-yl)furo[2,3-c]pyridin-7-amine

Product 1

HCID 667609052-(Imidazo[1,2-a]pyrazin-3-yl)-4-iodofuro[2,3-c]pyridin-7-amineYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Imidazo[1,2-a]pyrazin-3-yl)furo[2,3-c]pyridin-7-amine (0.018 g, 0.072 mmol) was dissolved in DMF (1 mL). NIS (0.024 g, 0.11 mmol) was added and the mixture was brought to 40° C. After 4 h, the reaction was cooled to room temperature. Water was added and the resulting solid was filtered off. The solid was dissolved in 2:1 methanol:DCM (−30 mL). To this solution was added aqueous sodium thiosulfate (0.5 mL) and the mixture was then concentrated. Purification by ISCO chromatography (0 to 20% methanol:DCM) afforded 0.018 g (67%) of the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 9.21 (dd, J=1.4, 4.7 Hz, 1 H), 9.17 (d, J=1.5 Hz, 1 H), 8.50 (s, 1 H), 8.14 (d, J=4.8 Hz, 1 H), 7.97 (s, 1 H), 7.27 (s, 1 H); MS (ESI): 378.14 [M+H]+.

Workup

  1. customwas brought to 40° C
  2. filtrationthe resulting solid was filtered off
  3. dissolutionThe solid was dissolved in 2:1 methanol
  4. additionTo this solution was added aqueous sodium thiosulfate (0.5 mL)
  5. concentrationthe mixture was then concentrated
  6. customPurification by ISCO chromatography (0 to 20% methanol:DCM)

Sources & evidence

ORD record
ord-7ae2d8817fee4167abd07d05e2a01433
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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