Hydrochloric Acid → 2-Amino-3-(4-chlorophenyl)-1-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-propan-1-one

HRID 1192306Notes

Reaction equation

HRID 1192306 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:9](=[O:25])[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[CH:23][NH:24][C:17]=23)[CH2:12][CH2:11]1)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[NH2:7][CH:8]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:9]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[CH:22]=[CH:23][NH:24][C:17]=23)[CH2:12][CH2:11]1)=[O:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67539194{1-(4-chlorobenzyl)-2-oxo-2-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 675380832-Amino-3-(4-chlorophenyl)-1-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-propan-1-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of {1-(4-chlorobenzyl)-2-oxo-2-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-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 4 hours. The solvent removed to afford the product 2-Amino-3-(4-chlorophenyl)-1-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-propan-1-one quantitatively. MS (ESI+) [M+H]+ 384.

Workup

  1. customThe solvent removed

Sources & evidence

ORD record
ord-9a1eab9b4aa246ee87d58cd40604a1bb
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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