1-(5-chlorothiophen-2-ylmethyl)3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine → 2-(2-{4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidin-1-yl}-ethoxy)-3-methoxy-benzoic acid

HRID 1437192Notes

Reaction equation

HRID 1437192 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:9]2)=[CH:4][CH:3]=1.C[O:24][C:25](=[O:38])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[C:27]=1[O:34][CH2:35][CH2:36]Cl>>[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([CH:17]3[CH2:18][CH2:19][N:20]([CH2:36][CH2:35][O:34][C:27]4[C:28]([O:32][CH3:33])=[CH:29][CH:30]=[CH:31][C:26]=4[C:25]([OH:38])=[O:24])[CH2:21][CH2:22]3)=[CH:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 179729751-(5-chlorothiophen-2-ylmethyl)3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridineHCID 688969452-(2-Chloroethoxy)-3-methoxy-benzoic acid methyl ester

Product 1

HCID 101747662-(2-{4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidin-1-yl}-ethoxy)-3-methoxy-benzoic acidYield 14%

Procedure

This compound was prepared following the procedure described in example 4, part E and F starting with 2 g (6 mmol) of 1-(5-chlorothiophen-2-ylmethyl)-3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine and 1.9 g (7.85 mmol) of 2-(2-chloroethoxy)-3-methoxy-benzoic acid methyl ester. After standard purification the overall yield was 14% (0.8 g).

Workup

  1. customThis compound was prepared
  2. customAfter standard purification the overall yield was 14% (0.8 g)

Sources & evidence

ORD record
ord-6979f72de6214f6b9355ddbeadda71bf
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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