3-Amino-6-bromopyrazine-2-carboxylic acid → Tert-butyl 1-(2-(3-amino-6-bromopyrazine-2-carboxamido)-4-methoxyphenyl)piperidin-4-ylcarbamate

HRID 69884

Reaction equation

HRID 69884 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]1.[NH2:24][C:25]1[C:26]([C:32](O)=[O:33])=[N:27][C:28]([Br:31])=[CH:29][N:30]=1>C(#N)C>[NH2:24][C:25]1[C:26]([C:32]([NH:1][C:2]2[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=2[N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH2:12][CH2:11]2)=[O:33])=[N:27][C:28]([Br:31])=[CH:29][N:30]=1

Participants

4

Reactant 2

HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acidHCID 69043362HCID 69043362, compound

Product 1

HCID 86669183Tert-butyl 1-(2-(3-amino-6-bromopyrazine-2-carboxamido)-4-methoxyphenyl)piperidin-4-ylcarbamateYield 7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following method 11, tert-butyl 1-(2-amino-4-methoxyphenyl)piperidin-4-ylcarbamate was coupled to 3-amino-6-bromopyrazine-2-carboxylic acid with TEA (3 eq) in ACN at 55° C. for 48 hours. Concentrated, triturated in cold ACN, filtered, and dried in vacuo yielding tert-butyl 1-(2-(3-amino-6-bromopyrazine-2-carboxamido)-4-methoxyphenyl)piperidin-4-ylcarbamate (7%). LCMS (m/z): 521.1 (MH+); LC Rt=3.63 min.

Workup

  1. concentrationConcentrated
  2. customtriturated in cold ACN
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ad9762d1a2d848578ffc5fb59556b8ac
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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