Ammonia → HCID 21111524, compound

HRID 1766822Notes

Reaction equation

HRID 1766822 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]3[O:16][C:17]([CH2:20]Cl)=[N:18][N:19]=3)=[CH:13][N:12]3[CH:22]=[CH:23][N:24]=[C:11]3[C:10]=2[Cl:25])=[C:4]([F:26])[CH:3]=1.[I-].[K+].[NH3:29]>O1CCCC1>[NH2:29][CH2:20][C:17]1[O:16][C:15]([C:14]2[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[F:26])=[C:10]([Cl:25])[C:11]3[N:12]([CH:22]=[CH:23][N:24]=3)[CH:13]=2)=[N:19][N:18]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 4875Potassium IodideHCID 21111547HCID 21111547, compound

Product 1

HCID 21111524HCID 21111524, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Bromo-2-fluoro-phenyl)-[8-chloro-6-(5-chloromethyl-[1,3,4]oxadiazol-2-yl)-imidazo[1,2-a]pyridin-7-yl]-amine (38 mg, 0.083 mmol) was dissolved in tetrahydrofuran (1 mL). Potassium iodide (14 mg, 0.083 mmol) was added and then ammonia (7 M solution in methanol, 0.30 mL, 2.08 mmol). The reaction mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography (gradient of 20:1 dichloromethane/methanol to 5:1) to yield the desired product (26 mg, 71%) as a yellow solid. MS ESI (+) m/z 437, 439 (M+, Cl, Br pattern) detected. 1H NMR (400 MHz, DMSO-d6) δ 9.35 (s, 1H), 8.33 (s, 1H), 8.17 (d, 1H), 7.70 (d, 1H), 7.51 (dd, 1H), 7.16 (d, 1H), 6.65 (t, 1H), 3.94 (s, 2H). 19F (376 MHz, DMSO-d6) −128.3 (t).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by flash column chromatography (gradient of 20:1 dichloromethane/methanol to 5:1)

Sources & evidence

ORD record
ord-a8ad7a9f839c4ee18e1450d6b6801705
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

Loading…