(S)-3-Amino-4-cyclopropyl-2-methyl-butan-2-ol → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid ((S)-1-cyclopropylmethyl-2-hydroxy-2-methyl-propyl)-amide

HRID 1477780Notes

Reaction equation

HRID 1477780 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][C@@H:22]([CH2:27][CH:28]1[CH2:30][CH2:29]1)[C:23]([CH3:26])([OH:25])[CH3:24]>>[CH:28]1([CH2:27][C@H: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])[C:23]([OH:25])([CH3:26])[CH3:24])[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 86674766(S)-3-Amino-4-cyclopropyl-2-methyl-butan-2-olHCID 866823246-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid

Product 1

HCID 715255776-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-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 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyrazine-2-carboxylic acid (Example 8d, 100 mg, 0.35 mmol) and (S)-3-amino-4-cyclopropyl-2-methyl-butan-2-ol (60.21 mg, 0.42 mmol) as starting materials, and isolated (50 mg, 34.72%) as white solid, LC-MS (UV peak area, ESI) 96.42%, 410.8 (M+H).

Workup

  1. customisolated (50 mg, 34.72%) as white solid, LC-MS (UV peak area, ESI) 96.42%, 410.8 (M+H)

Sources & evidence

ORD record
ord-6693a3be7ccb4eca8f1498c5db30e1ca
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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