[(Z)-[amino-[5-chloro-1-(4-methylphenyl)sulfonyl-2-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridin-4-yl]methylidene]amino] 1-hydroxycyclobutane-1-carboxylate → 1-(3-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,2,4-oxadiazol-5-yl)cyclobutanol

HRID 2362740Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:10][C:4]=2[C:3]=1/[C:27](=[N:29]/[O:30][C:31]([C:33]1([OH:37])[CH2:36][CH2:35][CH2:34]1)=O)/[NH2:28]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:27]2[N:28]=[C:31]([C:33]3([OH:37])[CH2:34][CH2:35][CH2:36]3)[O:30][N:29]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[N:8]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=3)(=[O:18])=[O:19])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (Z)-5-chloro-N′-(1-hydroxycyclobutanecarbonyloxy)-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carboximidamide (Example 138C) (53.8 mg, 0.099 mmol) in anhydrous toluene (1 mL) was heated for 4 hours at 110° C. under nitrogen. The reaction was concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel, eluting with a gradient of 40 to 50% ethyl acetate in hexanes, to provide the title compound. MS ESI(+) m/z 525.4 [M+H]+.

Workup

concentrationThe reaction was concentrated under reduced pressure
customthe residue was purified by flash chromatography on silica gel
washeluting with a gradient of 40 to 50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-699ab1e26d8344be8d9715831f9d5ae5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691810B2

Reaction notes

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