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

HRID 1436828Notes

Reaction equation

HRID 1436828 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 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-a9a5c5c07e6e4add882d9e36b7e63a83
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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