Hydrochloric Acid → (3-(4-chlorophenyl)pyrrolidin-3-yl)(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)methanone dihydrochloride

HRID 82381Notes

Reaction equation

HRID 82381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:20]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[C:29]5[C@H:36]([CH3:37])[CH2:35][CH2:34][C:30]=5[N:31]=[CH:32][N:33]=4)[CH2:24][CH2:23]3)=[O:21])[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[CH:4][CH:3]=1.[ClH:38]>C(Cl)Cl.O1CCOCC1>[ClH:1].[ClH:38].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:20]([N:22]3[CH2:23][CH2:24][N:25]([C:28]4[C:29]5[C@H:36]([CH3:37])[CH2:35][CH2:34][C:30]=5[N:31]=[CH:32][N:33]=4)[CH2:26][CH2:27]3)=[O:21])[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67339256HCID 67339256, compound

Product 1

HCID 67338547(3-(4-chlorophenyl)pyrrolidin-3-yl)(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)methanone dihydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3-(4-chlorophenyl)-3-(1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-4-carbonyl)pyrrolidine-1-carboxylate (25 mg, 0.048 mmol) in DCM (2.5 mL) was added to a 4.0M HCl solution in dioxane (0.8 mL). The mixture was stirred at room temperature overnight. The solvents were removed in vacuo to give (3-(4-chlorophenyl)pyrrolidin-3-yl)(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)methanone dihydrochloride (24 mg, 100%). LCMS (APCI+) [M+H]+ 426.2; Rt: 2.09.

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-d3731227e8434b7da67627a2c2746df5
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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