Dichloromethane → HCID 67434511, compound

HRID 2036565Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C@@H:10]([NH:12][C:13](=[O:29])[O:14][CH2:15][CH:16]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:11])=[C:4](NC2C=CC(F)=CC=2)[CH:3]=1.C(Cl)Cl.C([O-])(O)=O.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:8]=[C:9]([C@@H:10]([NH:12][C:13](=[O:29])[O:14][CH2:15][CH:16]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=4[C:23]4[C:28]3=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:11])[N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A Heterogeneous mixture of (S)-(9H-fluoren-9-yl)methyl 1-(4-fluoro-2-(4-fluorophenylamino)phenylamino)-1-oxopropan-2-ylcarbamate (3.500 g, 6.82 mmol) in acetic acid (45.4 mL) was heated at 100° C. with stirring. After 26 h, the mixture was cooled to rt and poured into DCM (100 mL) and satd. aq. NaHCO3 solution (100 mL). The aq. layer was removed and the organic layer was washed with satd. aq. NaHCO3 solution (100 mL×1), water (100 mL×1) and brine (100 mL×1), dried over MgSO4, filtered, and concentrated under reduced pressure to give (S)-(9H-fluoren-9-yl)methyl 1-(6-fluoro-1-(4-fluorophenyl)-1H-benzo[d]imidazol-2-yl)ethylcarbamate as a dark brown syrup: LC-MS (ESI) m/z 496.1 [M+H]+. Epimerization occurred during cyclization and the dark brown syrup was carried on crude without further purification.

Workup

temperaturethe mixture was cooled to rt
customThe aq. layer was removed
washthe organic layer was washed with satd
dry with materialaq. NaHCO3 solution (100 mL×1), water (100 mL×1) and brine (100 mL×1), dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d671f9f60df44841ae03247a958124cd
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

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