946484-82-8 → 2-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methyl}-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1677387Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[N:4]([Si](C(C)C)(C(C)C)C(C)C)[CH:3]=1.[C:33]([O:37][C:38]([N:40]1[CH2:44][CH2:43][CH2:42][C:41]1([CH:46]=[O:47])[CH3:45])=[O:39])([CH3:36])([CH3:35])[CH3:34]>>[C:33]([O:37][C:38]([N:40]1[CH2:44][CH2:43][CH2:42][C:41]1([CH:46]([OH:47])[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[NH:4][CH:3]=1)[CH3:45])=[O:39])([CH3:36])([CH3:35])[CH3:34]

Participants

Reactant 2

HCID 22456683946484-82-8

HCID 595405257-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 595410262-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methyl}-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

2-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methyl}-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester was prepared starting from 7-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine and 2-formyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (J. Org. Chem. 72 (15), 5608-5617, 2007) following the general procedures described in these Examples.

Sources & evidence

ORD record: ord-119bf6d7a6b44ab6be08b39241dec3e4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008298B2

Reaction notes

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