Pyrrolidin-1-amine monohydrochloride → 5-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid pyrrolidin-1-ylamide

HRID 1962997Notes

Reaction equation

HRID 1962997 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]([OH:23])=O)=[N:19][CH:20]=3)=[C:11]([CH2:24][OH:25])[O:10][N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:27][N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>>[N:28]1([NH:27][C:21]([C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:12]3[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[N:9][O:10][C:11]=3[CH2:24][OH:25])=[CH:20][N:19]=2)=[O:23])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 3017392Pyrrolidin-1-amine monohydrochlorideHCID 666443945-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid

Product 1

HCID 498044645-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid pyrrolidin-1-ylamideYield 23%

Procedure

As described for example 34b, 5-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid (100 mg, 0.29 mmol) was converted, using 1-aminopyrrolidine hydrochloride instead of S-(+)-1-amino-2-propanol, to the title compound (31 mg, 23%), which was obtained as a white solid. MS: m/e=413.2 [M+H]+.

Sources & evidence

ORD record
ord-11d0800735b7413d8bd1795442c966c1
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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