Potassium Phosphate, Tribasic → HCID 58052387, compound

HRID 2190195Notes

Reaction equation

Cl[C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][CH2:5][N:6]([C:11]1[N:16]=[C:15]2[O:17][C:18]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:19]([C:20]([NH:22][CH3:23])=[O:21])[C:14]2=[CH:13][C:12]=1[CH:31]1[CH2:33][CH2:32]1)[S:7]([CH3:10])(=[O:9])=[O:8].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:46]1COC[CH2:47]1.O>[Pd]>[CH:31]1([C:12]2[CH:13]=[C:14]3[C:19]([C:20]([NH:22][CH3:23])=[O:21])=[C:18]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[O:17][C:15]3=[N:16][C:11]=2[N:6]([CH2:5][CH2:4][C:3]2[CH:34]=[CH:35][CH:36]=[CH:37][C:2]=2[CH:46]=[CH2:47])[S:7]([CH3:10])(=[O:8])=[O:9])[CH2:32][CH2:33]1

Participants

Conditions

Temperature: 120 °C

Procedure

Combined 6-(N-(2-chlorophenethyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-(p-tolyl)furo[2,3-b]pyridine-3-carboxamide (38 mg, 0.071 mmol), Potassium phosphate Tribasic (nH2O) (244 mg, 1.059 mmol) and Pd-catalyst (42.4 mg, 0.071 mmol) in 3.4 mL 2:1 THF/water. Heated at 120° C. μwave for 20 min. Added water 50 mL and extracted 4× with EtOAc. Conc on vac. Taken up in DMF/ACN/drop of water Purified via HPLC C18 40-75% ACN/water (0.1% NH4OH)40 mL/min over 20 min to give 10.4 mg 5-cyclopropyl-N-methyl-2-(p-tolyl)-6-(N-(2-vinylphenethyl)methylsulfonamido)furo[2,3-b]pyridine-3-carboxamide

Workup

extractionAdded water 50 mL and extracted 4× with EtOAc
customPurified via HPLC

Sources & evidence

ORD record: ord-b183c424fa7445c4a5a905971379fac6
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324239B2

Reaction notes

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