1,1-Dimethylethyl 3-formyl-3-methyl-1-piperidinecarboxylate → 3-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methyl}-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 1677395Notes

Reaction equation

HRID 1677395 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[CH2:45][CH2:44][CH2:43][C:42]([CH:47]=[O:48])([CH3:46])[CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>>[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH2:43][C:42]([CH:47]([OH:48])[C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=4)[N:9]=3)[NH:4][CH:3]=2)([CH3:46])[CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34]

Participants

3

Reactant 2

HCID 222589171,1-Dimethylethyl 3-formyl-3-methyl-1-piperidinecarboxylateHCID 595405257-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 673455233-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methyl}-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

Procedure

3-{Hydroxy-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methyl}-3-methyl-piperidine-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 3-formyl-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (WO 2002024679) following general procedures as described in these Examples.

Sources & evidence

ORD record
ord-02a2ce6eeda6428b8f1f6dc05deb491f
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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