(S)-3-Amino-4-cyclopropyl-2-methyl-butan-2-ol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid ((S)-1-cyclopropylmethyl-2-hydroxy-2-methyl-propyl)-amide

HRID 1477781Notes

Reaction equation

HRID 1477781 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.[NH2:18][C@@H:19]([CH2:24][CH:25]1[CH2:27][CH2:26]1)[C:20]([CH3:23])([OH:22])[CH3:21]>>[CH:25]1([CH2:24][C@H:19]([NH:18][C:15]([C:7]2[CH:6]=[N:5][C:4]([CH:1]3[CH2:2][CH2:3]3)=[C:9]([O:10][CH2:11][CH:12]3[CH2:13][CH2:14]3)[N:8]=2)=[O:17])[C:20]([OH:22])([CH3:23])[CH3:21])[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 86674766(S)-3-Amino-4-cyclopropyl-2-methyl-butan-2-olHCID 866823315-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid

Product 1

HCID 866823325-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid ((S)-1-cyclopropylmethyl-2-hydroxy-2-methyl-propyl)-amide

Procedure

The title compound was synthesized in analogy to Example 15, using 5-cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid (Example 10 g, 100 mg, 0.43 mmol) and (S)-3-amino-4-cyclopropyl-2-methyl-butan-2-ol (87.83 mg, 0.64 mmol) as starting materials, and isolated (20 mg, 13.03%) as off white solid, LC-MS (UV peak area, ESI) 98.68%, 360.8 (M+H).

Workup

  1. customisolated (20 mg, 13.03%) as off white solid, LC-MS (UV peak area, ESI) 98.68%, 360.8 (M+H)

Sources & evidence

ORD record
ord-1885f22bf271491bbfe5cd1cc259d3d4
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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