(S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((R)-pyrrolidin-2-yl)ethanone → (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((S)-pyrrolidin-2-yl)ethanone

HRID 1916414Notes

Reaction equation

HRID 1916414 reaction equation
C(OC(N1CCC[C@@H]1[C@H](C1C=CC(Cl)=CC=1)C(O)=O)=O)(C)(C)C.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]([C@H:51]2[CH2:55][CH2:54][CH2:53][NH:52]2)[C:32]([N:34]2[CH2:39][CH2:38][N:37]([C:40]3[C:41]4[C@H:48]([CH3:49])[CH2:47][C@@H:46]([OH:50])[C:42]=4[N:43]=[CH:44][N:45]=3)[CH2:36][CH2:35]2)=[O:33])=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]([C@@H:51]2[CH2:55][CH2:54][CH2:53][NH:52]2)[C:32]([N:34]2[CH2:35][CH2:36][N:37]([C:40]3[C:41]4[C@H:48]([CH3:49])[CH2:47][C@@H:46]([OH:50])[C:42]=4[N:43]=[CH:44][N:45]=3)[CH2:38][CH2:39]2)=[O:33])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 58111328(S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((R)-pyrrolidin-2-yl)ethanoneHCID 66845132HCID 66845132, compound

Product 1

HCID 25170562(S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((S)-pyrrolidin-2-yl)ethanoneYield 264%

Procedure

Using procedures similar to those described in Example 1, Step 5, (S)-2-((R)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-2-(4-chlorophenyl)acetic acid (144 mg, 0.424 mmol) was converted to (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((R)-pyrrolidin-2-yl)ethanone (25 mg, 10%). LCMS (apci+) 456.0/458.0 [M+H]+; 1.93 minutes. Some (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((S)-pyrrolidin-2-yl)ethanone (66 mg, 28%) was also isolated.

Workup

  1. custom1.93 minutes

Sources & evidence

ORD record
ord-35df56bc9f804ebb99c0a80b171359c8
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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