Hydrochloric Acid → 2-(4-fluorophenyl)-3-(isopropylamino)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride

HRID 625058Notes

Reaction equation

HRID 625058 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[C:31]4[C@H:38]([CH3:39])[S:37][CH2:36][C:32]=4[N:33]=[CH:34][N:35]=3)[CH2:26][CH2:25]2)=[O:23])[CH2:10][N:11]([CH:19]([CH3:21])[CH3:20])C(=O)OC(C)(C)C)=[CH:5][CH:4]=1>CCOCC.C(Cl)Cl>[ClH:1].[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:10][NH:11][CH:19]([CH3:21])[CH3:20])[C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[C:31]4[C@H:38]([CH3:39])[S:37][CH2:36][C:32]=4[N:33]=[CH:34][N:35]=3)[CH2:26][CH2:25]2)=[O:23])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67459971tert-butyl 2-(4-fluorophenyl)-3-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate

Product 1

HCID 249497592-(4-fluorophenyl)-3-(isopropylamino)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochlorideYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

HCl (4N in dioxane) was added to a solution of tert-butyl 2-(4-fluorophenyl)-3-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (50 mg, 0.092 mmol) in Et2O (4 mL) and DCM (0.5 mL) at room temperature. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo. The residue was taken up into DCM (1 mL), and precipitated with Et2O (15 mL), and the solids were filtered under nitrogen to give 2-(4-fluorophenyl)-3-(isopropylamino)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride (30 mg, 63% yield) as a mixture of 2 diastereomers. LCMS (APCI+) [M+H]+ 444.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customprecipitated with Et2O (15 mL)
  3. filtrationthe solids were filtered under nitrogen

Sources & evidence

ORD record
ord-6c083cdf8772492480cd189178552fa3
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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