Hydrochloric Acid → (1R,3S)-3-[(3R)-tetrahydrofuran-3-yl]-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentanamine dihydrochloride

HRID 270617Notes

Reaction equation

HRID 270617 reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([C@:6]2([C:19]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=4)[CH2:23][CH2:22]3)=[O:20])[CH2:10][CH2:9][C@@H:8]([NH:11]C(=O)OC(C)(C)C)[CH2:7]2)[CH2:2]1.[ClH:37]>CCOCC>[ClH:37].[ClH:37].[O:1]1[CH2:5][CH2:4][C@H:3]([C@:6]2([C:19]([N:21]3[CH2:22][CH2:23][N:24]([C:27]4[CH:32]=[C:31]([C:33]([F:35])([F:34])[F:36])[CH:30]=[CH:29][N:28]=4)[CH2:25][CH2:26]3)=[O:20])[CH2:10][CH2:9][C@@H:8]([NH2:11])[CH2:7]2)[CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86641538tert-Butyl [(1R,3S)-3-[(3R)-Tetrahydrofuran-3-yl]-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentyl]carbamate

Product 1

HCID 68596876(1R,3S)-3-[(3R)-tetrahydrofuran-3-yl]-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentanamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl [(1R,3S)-3-[(3R)-tetrahydrofuran-3-yl]-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentyl]carbamate (260 mg, 0.51 mmol) was dissolved in a 2 M solution of of hydrogen chloride in ether (8 mL). After being stirred at room temperature overnight, the reaction mixture was concentrated under vacuum to provide the desired product (290 mg) as a light yellow solid. MS calculated for C20H27F3N4O2: (M+H) 413.2; found 413.0.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-bf5585bb80584908bcfa2001427ab8dd
Source dataset
uspto-grants-2008_11
Patent number
US07449467B2

Reaction notes

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