1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 90414773, compound

HRID 1526656Notes

Reaction equation

HRID 1526656 reaction equation
C([NH:9][C:10]1[O:11][C@@H:12]2[C@H:14]([C@@:15]([C:20]3[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=3[F:34])[C:23]([NH:25][C@@H:26]([CH3:30])[CH2:27][O:28][CH3:29])=[O:24])([CH:17]([F:19])[F:18])[N:16]=1)[CH2:13]2)(=O)C1C=CC=CC=1.N12CCCN=C1CCCCC2>CO>[NH2:9][C:10]1[O:11][C@@H:12]2[C@H:14]([C@@:15]([C:20]3[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=3[F:34])[C:23]([NH:25][C@@H:26]([CH3:30])[CH2:27][O:28][CH3:29])=[O:24])([CH:17]([F:19])[F:18])[N:16]=1)[CH2:13]2

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 90414755HCID 90414755, compound

Product 1

HCID 90414773HCID 90414773, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A flask was charged with 3-((1S,5R,6S)-3-benzamido-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4-fluoro-N—((S)-1-methoxypropan-2-yl)benzamide (0.3780 g, 0.795 mmol), 1,8-diazabicyclo-[5.4.0]undec-7-ene (0.143 ml, 0.954 mmol) and MeOH (7.95 ml). The reaction mixture was heated to 65° C. for 4 hours. The crude product was adsorbed onto a plug of silica gel and purified by flash chromatography, eluting with a gradient of 10% to 100% EtOAc:EtOH (75:25) in hexane, to provide the title compound (0.0563 g, 0.152 mmol, 19.07% yield).

Workup

  1. custompurified by flash chromatography
  2. washeluting with a gradient of 10% to 100% EtOAc:EtOH (75:25) in hexane

Sources & evidence

ORD record
ord-44177d0a73dd4513bac7d7839ac9c872
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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