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

HRID 1477776Notes

Reaction equation

HRID 1477776 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([C:15]([OH:17])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.Cl.[CH3:19][C:20]1[O:24][N:23]=[C:22]([C:25]2([NH2:29])[CH2:28][CH2:27][CH2:26]2)[N:21]=1>>[CH3:19][C:20]1[O:24][N:23]=[C:22]([C:25]2([NH:29][C:15]([C:7]3[CH:6]=[N:5][C:4]([CH:1]4[CH2:2][CH2:3]4)=[C:9]([O:10][CH2:11][CH:12]4[CH2:13][CH2:14]4)[N:8]=3)=[O:17])[CH2:28][CH2:27][CH2:26]2)[N:21]=1

Participants

3

Reactant 2

HCID 429590521-(5-Methyl-1,2,4-oxadiazol-3-yl)cyclobutan-1-amine hydrochlorideHCID 866823315-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid

Product 1

HCID 715255745-Cyclopropyl-6-cyclopropylmethoxy-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 5-cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid (Example 10 g, 100 mg, 0.43 mmol) and 1-(5-methyl-1,2,4-oxadiazol-3-yl)-cyclobutanamine (CAN 1170897-128-5, 98.07 mg, 0.64 mmol) as starting materials, and isolated (50 mg, 31.67%) as off white solid; LC-MS (UV peak area, ESI) 99.91%, 370.0 (M+H).

Workup

  1. customisolated (50 mg, 31.67%) as off white solid

Sources & evidence

ORD record
ord-895fff97218b4fd5b6adbb814c8b3f4f
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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