Trifluoroacetic acid → (S)-2-Amino-2-cyclohexyl-1-{(S)-2-[2-(1H-indole-3-yl)-pyridin-4-yl]-pyrrolidin-1-yl}-ethanone

HRID 1667627Notes

Reaction equation

HRID 1667627 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH:17]=1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH:17]=1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66889931((S)-1-Cyclohexyl-2-{(S)-2-[2-(1H-indol-3-yl)-pyridin-4-yl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 66889854(S)-2-Amino-2-cyclohexyl-1-{(S)-2-[2-(1H-indole-3-yl)-pyridin-4-yl]-pyrrolidin-1-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ((S)-1-Cyclohexyl-2-{(S)-2-[2-(1H-indol-3-yl)-pyridin-4-yl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester (120 mg, 0.24 mmol) in DCM (2 mL) is added TFA (2 mL). After stirring at room temperature for 1 h, the reaction mixture is concentrated down to give crude (S)-2-Amino-2-cyclohexyl-1-{(S)-2-[2-(1H-indole-3-yl)-pyridin-4-yl]-pyrrolidin-1-yl}-ethanone, which is used in next step without purification.

Workup

  1. concentrationthe reaction mixture is concentrated down

Sources & evidence

ORD record
ord-c6077160a4f6488894450aad69e63f99
Source dataset
uspto-grants-2011_10
Patent number
US08044209B2

Reaction notes

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