Phosphorus sulfide (P2S5) → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(1,3,4-thiadiazol-2-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79349

Reaction equation

[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([NH:26][NH:27][CH:28]=O)=O)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[N:32]=2)[N:4]=1)[CH3:2].C[Si](C)(C)O[Si](C)(C)C.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:48]>C1(C)C=CC=CC=1.O1CCOCC1>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]4[S:48][CH:28]=[N:27][N:26]=4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[N:32]=2)[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-formylhydrazinecarbonyl)imidazo[1,2-a]pyridine-3-carboxamide (36 mg, 0.073 mmol) in toluene/dioxane (1 mL/1 mL) was added hexamethyldisiloxane (71 mg, 0.44 mmol) and P2S5 (81 mg, 0.36 mmol). The reaction mixture was sealed and heated in a microwave reactor to 110° C. for 3 hours. The mixture was then concentrated under reduced pressure and the residue was purified by silica gel chromatography (DCM/MeOH 10:1) to provide the final product (1.5 mg). MS (ES+APCI) m/z=495 (M+H).

Workup

customThe reaction mixture was sealed
concentrationThe mixture was then concentrated under reduced pressure
customthe residue was purified by silica gel chromatography (DCM/MeOH 10:1)

Sources & evidence

ORD record: ord-e51ef1358ef948d0ac0002c2f20a5bd7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Linked notes

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