(S)-2-amino-2,3-dimethylbutan-1-ol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-1,2-dimethyl-propyl)-amide

HRID 1477803Notes

Reaction equation

HRID 1477803 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@@:19]([CH3:25])([CH:22]([CH3:24])[CH3:23])[CH2:20][OH:21]>>[OH:21][CH2:20][C@:19]([NH:18][C:15]([C:7]1[CH:6]=[N:5][C:4]([CH:1]2[CH2:2][CH2:3]2)=[C:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[N:8]=1)=[O:17])([CH3:25])[CH:22]([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 14919272(S)-2-amino-2,3-dimethylbutan-1-olHCID 866823315-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid

Product 1

HCID 715260375-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-1,2-dimethyl-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, 0.42 mmol) and (2S)-2-amino-2,3-dimethyl-1-butanol (CAN 956102-64-0, 107.06 mg, 0.64 mmol) as starting materials, and isolated (25 mg, 16.04%) as off white sticky solid, LC-MS (UV peak area, ESI) 90.02%, 334.4 (M+H).

Workup

  1. customisolated (25 mg, 16.04%) as off white sticky solid, LC-MS (UV peak area, ESI) 90.02%, 334.4 (M+H)

Sources & evidence

ORD record
ord-3ca2b9ad3f3249df9215f38ecd87fddc
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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