HCID 67479577, compound → HCID 67480057, compound

HRID 1752295Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1)(=O)[CH3:2]>CC(O)=O>[Cl:11][C:7]1[C:6]2[N:12]([C@@H:13]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]3)[C:1]([CH3:2])=[N:4][C:5]=2[CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Crude (R)-tert-butyl 3-((2-acetamido-6-chlorophenyl)amino)pyrrolidine-1-carboxylate (148 mg) was dissolved in glacial HOAc (20 mL) and heated at 70° C. for 1 day. The mixture was concentrated. The residue was taken up in EtOAc (100 mL), washed with satd aq NaHCO3 (10 mL) and brine (10 mL), and dried over Na2SO4. Removal of the solvent left a brown oil (133 mg) which was purified by chromatography on a 12-g silica gel cartridge eluted with a 0-100% EtOAc in hexanes gradient to afford (R)-tert-butyl 3-(7-chloro-2-methyl-1H-benzo[d]imidazol-1-yl)pyrrolidine-1-carboxylate (59 mg, 18%) as a brown oil. LC-MS Method 1 tR=1.42 min, m/z=336.

Workup

concentrationThe mixture was concentrated
washwashed with satd aq NaHCO3 (10 mL) and brine (10 mL)
dry with materialdried over Na2SO4
customRemoval of the solvent
waitleft a brown oil (133 mg) which
customwas purified by chromatography on a 12-g silica gel cartridge
washeluted with a 0-100% EtOAc in hexanes gradient

Sources & evidence

ORD record: ord-3b05b56c9711499e9e1ec1a6004884fc
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163012B2

Reaction notes

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