1-(5-Methyl-1,2,4-oxadiazol-3-yl)cyclobutan-1-amine hydrochloride → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid [1-(5-methyl-[1,2,4]oxadiazol-3-yl)-cyclobutyl]-amide

HRID 1477773Notes

Reaction equation

HRID 1477773 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.Cl.[CH3:22][C:23]1[O:27][N:26]=[C:25]([C:28]2([NH2:32])[CH2:31][CH2:30][CH2:29]2)[N:24]=1>>[CH3:22][C:23]1[O:27][N:26]=[C:25]([C:28]2([NH:32][C:12]([C:10]3[CH:9]=[N:8][C:7]([N:15]4[CH2:18][C:17]([F:20])([F:19])[CH2:16]4)=[C:6]([O:5][CH2:4][CH:1]4[CH2:2][CH2:3]4)[N:11]=3)=[O:14])[CH2:31][CH2:30][CH2:29]2)[N:24]=1

Participants

3

Reactant 2

HCID 429590521-(5-Methyl-1,2,4-oxadiazol-3-yl)cyclobutan-1-amine hydrochlorideHCID 866823246-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid

Product 1

HCID 715255716-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid [1-(5-methyl-[1,2,4]oxadiazol-3-yl)-cyclobutyl]-amide

Procedure

The title compound was synthesized in analogy to Example 8e, using 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid (Example 8d, 100 mg, 0.35 mmol) and 1-(5-methyl-1,2,4-oxadiazol-3-yl)-cyclobutanamine (CAN 1170897-128-5, 64.42 mg, 0.42 mmol) as starting materials, and isolated (25 mg, 16.95%) as off white solid; LC-MS (UV peak area, ESI) 99.10%, 421.4 (M+H).

Workup

  1. customisolated (25 mg, 16.95%) as off white solid

Sources & evidence

ORD record
ord-93240d2a6dc441fc80489fa4e5d971f4
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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