[(S)-1-(3-Phenylaminopyridin-2-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester → [(S)-1-(1-Phenyl-1H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl ester

HRID 242973Notes

Reaction equation

[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[C:17]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][N:13]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:10]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]2[C:12]([N:11]=1)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of [(S)-1-(3-phenylaminopyridin-2-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (980 mg, 2.75 mmol) in AcOH (25 mL) was heated for 10 h at 75° C. under a nitrogen atmosphere. The volatiles were removed in vacuo and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo to afford the title compound as a light brown foam (920 mg, 99%). LCMS (Method C): RT 2.88 min [M+H]+ 339.3.

Workup

customThe volatiles were removed in vacuo
customthe resulting residue partitioned between DCM
extractionThe aqueous phase was further extracted with DCM (×3)
washthe combined organic fractions washed with water
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c2e6c14aae4f4c48accf7912ce755334
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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