Benzene, 2-ethynyl-1,4-difluoro- → HCID 131734199, compound

HRID 1497353Notes

Reaction equation

HRID 1497353 reaction equation
BrC1C=NC([N:8]2[CH:12]3[CH2:13][CH2:14][CH2:15][CH:11]3[N:10](CCOC)[C:9]2=[O:20])=NC=1.[C:21]([C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[F:30])#[CH:22]>>[F:30][C:24]1[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=1[C:21]1[C:12]([C:11]#[CH:15])=[N:8][C:9]([CH:14]2[CH2:15][CH:11]3[NH:10][C:9](=[O:20])[NH:8][CH:12]3[CH2:13]2)=[N:10][CH:22]=1

Participants

3

Reactant 2

HCID 50998805Benzene, 2-ethynyl-1,4-difluoro-HCID 90039063HCID 90039063, compound

Product 1

HCID 131734199HCID 131734199, compound

Procedure

The title compound was prepared in accordance with the general method of Example 1, step 5 starting from (rac)-1-(5-bromopyrimidin-2-yl)-3-(2-methoxy-ethyl)-hexahydro-cyclopenta[d]imidazol-2(1H)-one (Example 5, step 3) and 1-ethynyl-2,5-difluorobenzene to yield racemic material ((+/−)-(3aRS,6aSR)-1-(2-methoxy-ethyl)-3-(5-(2,5-difluoro-phenyl-ethynyl-pyrimidin-2-yl)-hexahydro-cyclopentaimidazol-2-one as a light brown solid; MS: m/e=399.2 (M+H+). Separation using chiral HPLC and similar separation conditions as described in example 1 yielded the enantiomerically pure enantiomers (−)-(3aR,6aS)-1-(2-methoxy-ethyl)-3-(5-(2,5-difluoro-phenylethynyl-pyrimidin-2-yl)-hexahydro-cyclopentaimidazol-2-one as an off-white solid; MS: m/e=399.2 (M+H+) and (+)-(3aS,6aR)-1-(2-methoxy-ethyl)-3-(5-(2,5-difluoro-phenylethynyl-pyrimidin-2-yl)-hexahydro-cyclopentaimidazol-2-one as a light yellow oil which solidified on standing; MS: m/e=399.2 (M+H+).

Sources & evidence

ORD record
ord-386604d544a74ac1814e08ffc4527aa3
Source dataset
uspto-grants-2015_12
Patent number
US09199971B2

Reaction notes

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