3-Amino-6-bromopyrazine-2-carboxylic acid → HCID 86669182, compound

HRID 69883

Reaction equation

HRID 69883 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.[NH2:29][C:30]1[C:31]([C:37](O)=[O:38])=[N:32][C:33]([Br:36])=[CH:34][N:35]=1>C(#N)C>[NH2:29][C:30]1[C:31]([C:37]([NH:1][C:2]2[CH:7]=[C:6]([C:8](=[O:15])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:5]=[CH:4][C:3]=2[N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[O:38])=[N:32][C:33]([Br:36])=[CH:34][N:35]=1

Participants

4

Reactant 2

HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acidHCID 68161607Tert-butyl 4-(2-amino-4-benzoylphenyl)piperazine-1-carboxylate

Product 1

HCID 86669182HCID 86669182, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following method 11, tert-butyl 4-(2-amino-4-benzoylphenyl)piperazine-1-carboxylate was coupled to 3-amino-6-bromopyrazine-2-carboxylic acid with TEA (1.5 eq) in ACN at 55° C. for 48 hours. Concentrated, triturated in cold ACN, filtered, and dried in vacuo yielding tert-butyl 4-(2-(3-amino-6-bromopyrazine-2-carboxamido)-4-benzoylphenyl)piperazine-1-carboxylate (50%). LCMS (m/z): 581.1 (MH+); LC Rt=4.00 min.

Workup

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

Sources & evidence

ORD record
ord-8f947026be30409d8523c55ddf748b24
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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