(R)-3-fluoro-4-(7-oxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile → 4-((5R)-8-(4-fluorophenyl)-8-hydroxy-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile

HRID 2036035

Reaction equation

HRID 2036035 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C@@H]1N2C=NC=C2C(=O)C1)C#N.[O:19]=[C:20]1[CH2:25][CH2:24][C@H:23]([C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=2)[N:22]2[CH:34]=[N:35][CH:36]=[C:21]12>>[F:1][C:2]1[CH:3]=[CH:4][C:7]([C:20]2([OH:19])[CH2:25][CH2:24][C@H:23]([C:26]3[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=3)[N:22]3[CH:34]=[N:35][CH:36]=[C:21]23)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 67216150(R)-3-fluoro-4-(7-oxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrileHCID 67216373(R)-4-(8-oxo-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile

Product 1

HCID 532371184-((5R)-8-(4-fluorophenyl)-8-hydroxy-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile

Procedure

Following compounds are prepared using similar procedure as example 1-1 through example 1-7 using either 3-fluoro-4-((R)-7-oxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-benzonitrile or (R)-4-(8-oxo-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile with appropriate reagents and conditions: Note when possible, separation of diastereomers were individually achieved with preparation plates, flash chromatography, prep-LCMS, HPLC, and or using HPLC CHIRALPAK® HPLC columns (such as AD, OJ, OD, etc.) which are purchased from Daicel.

Workup

  1. customare prepared
  2. customseparation of diastereomers
  3. customwere individually achieved with preparation plates, flash chromatography

Sources & evidence

ORD record
ord-de47e83f1843440aa1e8bd0b8009ccfc
Source dataset
uspto-grants-2013_11
Patent number
US08575160B2

Linked notes

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