2-(1,3-Benzodioxol-5-yloxy)pyridine-3-carboxylic acid → (+)-2-[4-({[2-(Benzo[2,1,3]thiadiazol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-propionic acid tert-butyl ester

HRID 350985Notes

Reaction equation

HRID 350985 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[CH:9]=[C:8]([O:10][C:11]3[N:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13]([OH:15])=O)[CH:7]=[CH:6][C:5]=12.[C:20]([O:24][C:25](=[O:38])[CH:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH2:36])=[C:31]([F:37])[CH:30]=1)[CH3:27])([CH3:23])([CH3:22])[CH3:21].O1C2C=CC(OC3N=CC=CC=3C(O)=O)=CC=2OC1.COC(=O)COC1C=CC(CN)=C(F)C=1>>[C:20]([O:24][C:25](=[O:38])[CH:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH:36][C:13]([C:12]2[C:11]([O:10][C:8]3[CH:7]=[CH:6][C:5]4=[N:1][S:2][N:3]=[C:4]4[CH:9]=3)=[N:19][CH:18]=[CH:17][CH:16]=2)=[O:15])=[C:31]([F:37])[CH:30]=1)[CH3:27])([CH3:21])([CH3:22])[CH3:23]

Participants

5

Reactant 4

HCID 27368792-(1,3-Benzodioxol-5-yloxy)pyridine-3-carboxylic acidHCID 18174008Methyl 2-[4-(aminomethyl)-3-fluorophenoxy]acetateHCID 226101592-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acidHCID 23529364(+)-2-(4-Aminomethyl-3-fluoro-phenoxy)-propionic acid tert-butyl ester

Product 1

HCID 23529360(+)-2-[4-({[2-(Benzo[2,1,3]thiadiazol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-propionic acid tert-butyl ester

Procedure

The compound of Formula (5.0.27) was prepared in a manner analogous to that described in Preparation 20, substituting 2-(benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid and (+)-2-(4-aminomethyl-3-fluoro-phenoxy)-propionic acid tert-butyl ester for the corresponding 2-(benzo-[1,3]-dioxol-5-yloxy)-nicotinic acid and (4-aminomethyl-3-fluoro-phenoxy)-acetic acid methyl ester materials, respectively.

Workup

  1. customthat described in Preparation 20

Sources & evidence

ORD record
ord-1aab8af1c7a04bd29b59d1e2942d1556
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

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