HCID 10387575, compound → HCID 10451378, compound

HRID 2221499Notes

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.[Cl:32][C:33]1[CH:56]=[C:55]([F:57])[CH:54]=[CH:53][C:34]=1[O:35][CH2:36][C:37]1[C:41]2[CH:42]=[N:43][C:44]([C:46]([O:48]CC)=O)=[CH:45][C:40]=2[N:39]([CH2:51][CH3:52])[CH:38]=1.ClC1C(O)=C(C=C(F)C=1)CC1C2C=NC(C(OCC)=O)=CC=2N(CC)C=1>>[Cl:32][C:33]1[CH:56]=[C:55]([F:57])[CH:54]=[CH:53][C:34]=1[O:35][CH2:36][C:37]1[C:41]2[CH:42]=[N:43][C:44]([C:46]([NH:21][OH:22])=[O:48])=[CH:45][C:40]=2[N:39]([CH2:51][CH3:52])[CH:38]=1

Participants

Reactant 3

HCID 10387575HCID 10387575, compound

HCID 21892203HCID 21892203, compound

HCID 21892229HCID 21892229, compound

Product 1

HCID 10451378HCID 10451378, compound

Procedure

Ethyl 3-(2-chloro-4-fluoro-phenoxymethyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate and ethyl 3-(3-chloro-5-fluoro-2-hydroxy-benzyl)-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-chloro-4-fluorophenol using methods similar to step (e) of Example 54. (b) 3-(2-Chloro-4-fluoro-phenoxymethyl)-1-ethyl-N-hydroxy-1H-pyrrolo[3,2-c]pyridine-6-carboxamide. The title compound can be prepared from a mixture of ethyl 3-(2-chloro-4-fluoro-phenoxymethyl)-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate and ethyl 3-(3-chloro-5-fluoro-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-7559d06e805f45ea9732ccb4d484b88e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368571B2

Reaction notes

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