2-Amino-2-cyclopropylethanol → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid (1-cyclopropyl-2-hydroxy-ethyl)-amide

HRID 1477785Notes

Reaction equation

HRID 1477785 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[N:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:3][CH2:2]1.[NH2:21][CH:22]([CH:25]1[CH2:27][CH2:26]1)[CH2:23][OH:24]>>[CH:25]1([CH:22]([NH:21][C:12]([C:10]2[CH:9]=[N:8][C:7]([N:15]3[CH2:18][C:17]([F:20])([F:19])[CH2:16]3)=[C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[N:11]=2)=[O:14])[CH2:23][OH:24])[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 545935222-Amino-2-cyclopropylethanolHCID 866823246-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid

Product 1

HCID 715256686-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid (1-cyclopropyl-2-hydroxy-ethyl)-amide

Procedure

The title compound was synthesized in analogy to Example 15, using 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid (Example 8d, 100 mg, 0.35 mmol) and β-amino-cyclopropaneethanol (CAN 776315-67-4, 78.94 mg, 0.53 mmol) as starting materials, and isolated (20 mg, 14.91%) as light brown solid; LC-MS (UV peak area, ESI) 97.84%, 368.9 (M+H).

Workup

  1. customisolated (20 mg, 14.91%) as light brown solid

Sources & evidence

ORD record
ord-b1d3aeb5500d47ffa3201c6dc5cfcab3
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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