(2S)-2-Amino-N,3,3-trimethylbutanamide → 5-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

HRID 1477778Notes

Reaction equation

HRID 1477778 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]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:20]([NH:22][CH3:23])=[O:21]>>[CH3:25][C:24]([CH3:27])([CH3:26])[C@H: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])[C:20](=[O:21])[NH:22][CH3:23]

Participants

3

Reactant 2

HCID 445856(2S)-2-Amino-N,3,3-trimethylbutanamideHCID 866823315-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid

Product 1

HCID 715254015-Cyclopropyl-6-cyclopropylmethoxy-pyrazine-2-carboxylic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-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 (S)-2-amino-3,3,N-trimethyl-butyramide (CAN 89226-12-0, 106.7 mg, 0.64 mmol) as starting materials, and isolated (45 mg, 29.4%) as off white solid, LC-MS (UV peak area, ESI) 100%, 361.4 (M+H).

Workup

  1. customisolated (45 mg, 29.4%) as off white solid, LC-MS (UV peak area, ESI) 100%, 361.4 (M+H)

Sources & evidence

ORD record
ord-747ad1831f3e43519bb5f8d6a13ed421
Source dataset
uspto-grants-2016_08
Patent number
US09403808B2

Reaction notes

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