Hydrochloric Acid → 4-{4-[2-Amino-3-(4-chlorophenyl)-propionyl]-piperazin-1-yl}-thieno[3,2-d]pyrimidine-6-carbonitrile dihydrochloride

HRID 1192315Notes

Reaction equation

HRID 1192315 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[S:25][C:24]([C:26]#[N:27])=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[ClH:37]>C(Cl)Cl.O1CCOCC1>[ClH:35].[ClH:37].[NH2:7][CH:8]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[C:18]3[S:25][C:24]([C:26]#[N:27])=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:15][CH2:16]1)=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67539318{1-(4-Chlorobenzyl)-2-[4-(6-cyanothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 675395244-{4-[2-Amino-3-(4-chlorophenyl)-propionyl]-piperazin-1-yl}-thieno[3,2-d]pyrimidine-6-carbonitrile dihydrochlorideYield 44%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of {1-(4-chlorobenzyl)-2-[4-(6-cyanothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester in DCM (4 mL) was added HCl in Dioxane (4M, 1 mL). The mixture was stirred at room temperature for 10 hours. The solvent was removed and the residue was subject to purification by HPLC to afford the product 4-{4-[2-Amino-3-(4-chlorophenyl)-propionyl]-piperazin-1-yl}-thieno[3,2-d]pyrimidine-6-carbonitrile dihydrochloride (12 mg, 44%). MS (ESI+) [M+H]+ 427.

Workup

  1. customThe solvent was removed
  2. customthe residue was subject to purification by HPLC

Sources & evidence

ORD record
ord-6bdbfe77a32946e4889831a23770e96d
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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