4-{-4-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester → 2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1677376Notes

Reaction equation

HRID 1677376 reaction equation
C(N1CCN([C:10]2[CH:11]=[C:12]([C:16]3[N:17]=[C:18]4[C:24](C(=O)C(C)(C)C)=[CH:23][NH:22][C:19]4=[N:20][CH:21]=3)[CH:13]=[CH:14][CH:15]=2)CC1)(=O)C.[C:31]([O:35]C(N1CCN(C2C=CC(C3N=C4C(C(=O)C(C)(C)C)=CNC4=NC=3)=CC=2)CC1)=O)(C)(C)C.[C:65]([O:69]C(N1CCN(C2C=CC=C(C3N=C4C(C(=O)C(C)(C)C)=CNC4=NC=3)C=2)CC1)=O)(C)(C)C.[C:99](OC(=O)C)(=[O:101])C.CN(C=O)C>>[CH3:31][O:35][C:14]1[CH:13]=[C:12]([C:16]2[N:17]=[C:18]3[CH:24]=[CH:23][NH:22][C:19]3=[N:20][CH:21]=2)[CH:11]=[C:10]([O:101][CH3:99])[C:15]=1[O:69][CH3:65]

Participants

5

Reactant 4

HCID 442062674-{-4-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl esterHCID 497643134-{3-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl esterHCID 595406201-{2-[3-(4-Acetyl-piperazin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-oneHCID 86761394acetic anhydride DMF

Product 1

HCID 595406852-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Procedure

1-{2-[3-(4-Acetyl-piperazin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one, MP=238.0-239.0, (M+H)+=406, (prepared, respectively, from 4-{-4-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester or 4-{3-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester by reaction with acetic anhydride/DMF at 0° C.); and

Sources & evidence

ORD record
ord-7248ab093d024e389828ac415bffdaa6
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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