(1-Aminocyclopropyl)methanol → 4-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1-hydroxymethyl-cyclopropyl)-amide

HRID 1480109Notes

Reaction equation

HRID 1480109 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([N:12]3[CH2:15][C:14]([F:17])([F:16])[CH2:13]3)=[CH:10][N:9]=[C:8]([C:18]([OH:20])=O)[CH:7]=2)[CH2:3][CH2:2]1.[NH2:21][C:22]1([CH2:25][OH:26])[CH2:24][CH2:23]1>>[OH:26][CH2:25][C:22]1([NH:21][C:18]([C:8]2[CH:7]=[C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:11]([N:12]3[CH2:13][C:14]([F:16])([F:17])[CH2:15]3)=[CH:10][N:9]=2)=[O:20])[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 14146220(1-Aminocyclopropyl)methanolHCID 902040914-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

Product 1

HCID 902149564-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1-hydroxymethyl-cyclopropyl)-amide

Procedure

The title compound was synthesized in analogy to Example 24d, using 4-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 53e) and (1-aminocyclopropyl)methanol (CAN 107017-72-1) as starting materials and isolated (85 mg, 51%) as a waxy solid; MS (ESI, m/z): 354.3 (M+H+).

Workup

  1. customisolated (85 mg, 51%) as a waxy solid

Sources & evidence

ORD record
ord-236423607e4341729c6f7e2c56778bc4
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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