Methyl iodide → HCID 59153115, compound

HRID 1095849Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15][S:16]([C:19]3[CH:20]=[N:21][C:22]([Cl:26])=[C:23]([Br:25])[CH:24]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2].CI.[C:30](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([N:15]([S:16]([C:19]3[CH:20]=[N:21][C:22]([Cl:26])=[C:23]([Br:25])[CH:24]=3)(=[O:18])=[O:17])[CH3:30])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of [(R)-4-(5-bromo-6-chloro-pyridine-3-sulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (prepared as described above in example 2-1, 1st step) (740 mg, 1.55 mmol) in acetonitrile (15 mL) was added methyl iodide (655 mg, 4.65 mmol) and potassium carbonate (641 mg, 4.65 mmol). The reaction mixture was stirred at 65° C. for 5 hours, then cooled to room temperature and filtered through a glass funnel. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (gradient elution, 0-10% methanol in dichloromethane) to afford {(R)-4-[(5-bromo-6-chloro-pyridine-3-sulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (680 mg, 89%) as a yellow solid. Ms cald. for C17H20BrClN4O4S 490, obsd. (ESI+) [(M+H)+] 491.

Workup

temperaturecooled to room temperature
filtrationfiltered through a glass funnel
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by column chromatography (gradient elution, 0-10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-dc8c17f5253444b3869c895074cbe91f
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138208B2

Reaction notes

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