HCID 10387575, compound → HCID 10090221, compound

HRID 2221503Notes

Reaction equation

C(OCC1C2C(=CN=C(C([NH:21][OH:22])=O)C=2)N(CC2C=CC(F)=CC=2F)C=1)C1C=CC=CC=1.FC1(F)C(F)=CC=C(OCC2C3C=NC(C(OCC)=O)=CC=3N(CC)C=2)C1.[F:59][C:60]1[C:61]([OH:85])=[C:62]([CH:80]=[C:81]([F:84])[C:82]=1[F:83])[CH2:63][C:64]1[C:68]2[CH:69]=[N:70][C:71]([C:73]([O:75]CC)=O)=[CH:72][C:67]=2[N:66]([CH2:78][CH3:79])[CH:65]=1>>[CH2:78]([N:66]1[C:67]2[CH:72]=[C:71]([C:73]([NH:21][OH:22])=[O:75])[N:70]=[CH:69][C:68]=2[C:64]([CH2:63][C:62]2[CH:80]=[C:81]([F:84])[C:82]([F:83])=[C:60]([F:59])[C:61]=2[OH:85])=[CH:65]1)[CH3:79]

Participants

Reactant 3

HCID 10387575HCID 10387575, compound

HCID 21892185HCID 21892185, compound

HCID 68454430HCID 68454430, compound

Product 1

HCID 10090221HCID 10090221, compound

Procedure

Ethyl 3-(3,4,5-trifluoro-2-hydroxybenzyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate. The title compound can be prepared from ethyl 3-hydroxymethyl-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate and 2,3,4-trifluorophenol using a methods similar to that set forth in Example 55. (b) 1-Ethyl-N-hydroxy 3-(3,4,5-trifluoro-2-hydroxybenzyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxamide. The title compound can be prepared from a mixture of ethyl 3-(3,3,4-trifluoro-phenoxymethyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate and ethyl 3-(3,4,5-trifluoro-2-hydroxy-benzyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate in a manner similar to step (e) of Example 11. Purification by HPLC can provide the pure title compound.

Sources & evidence

ORD record: ord-7e2ab7e4ae92493395dfb5a26d65decf
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368571B2

Reaction notes

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