1,2-Dichloroethane → 5-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indazole

HRID 2189802Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=O)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(N(CC)CC)C.O.OC1C2N=NNC=2C=CC=1.C(Cl)CCl.O[NH:38][C:39]([C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[NH:46][N:45]=[CH:44]2)=[NH:40]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:14][N:38]=[C:39]([C:41]3[CH:42]=[C:43]4[C:47](=[CH:48][CH:49]=3)[NH:46][N:45]=[CH:44]4)[N:40]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylic acid (D31) (350 mg, 1.623 mmol), triethylamine (328 mg, 452 μl, 3.25 mmol), hydroxybenzotriazole hydrate (298 mg, 1.95 mmol), EDC (373 mg, 1.95 mmol) and N-hydroxy-1H-indazole-5-carboximidamide (D2) (430 mg, 2.43 mmol) in DMF (5 ml) was stirred at 50° C. for 4 days. The reaction mixture was cooled to room temperature and diluted with EtOAc (25 ml). The organic layer was washed with a saturated NaHCO3 aqueous solution, water then brine. The organic phase was dried and concentrated in vacuo to give the title compound (334 mg, 58%) as a light red solid which was used in next step without further purification. MS (ES) C17H14ClN5O2 requires 355, found 356 [M+H]+

Workup

temperatureThe reaction mixture was cooled to room temperature
washThe organic layer was washed with a saturated NaHCO3 aqueous solution, water
customThe organic phase was dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8b33ce14ee6c4056947d10d545b82399
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324254B2

Reaction notes

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