3-Amino-6-bromopyrazine-2-carboxylic acid → HCID 86669181, compound

HRID 69882

Reaction equation

HRID 69882 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][CH2:19][CH:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17]1.[NH2:30][C:31]1[C:32]([C:38](O)=[O:39])=[N:33][C:34]([Br:37])=[CH:35][N:36]=1>C(#N)C>[NH2:30][C:31]1[C:32]([C:38]([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][CH2:19][CH:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH2:17]2)=[O:39])=[N:33][C:34]([Br:37])=[CH:35][N:36]=1

Participants

4

Reactant 2

HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acidHCID 690437681,1-Dimethylethyl N-[1-(2-amino-4-benzoylphenyl)-3-piperidinyl]carbamate

Product 1

HCID 86669181HCID 86669181, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following method 11, tert-butyl 1-(2-amino-4-benzoylphenyl)piperidin-3-ylcarbamate 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 1-(2-(3-amino-6-bromopyrazine-2-carboxamido)-4-benzoylphenyl)piperidin-3-ylcarbamate (30%). LCMS (m/z): 595.1 (MH+); LC Rt=3.87 min.

Workup

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

Sources & evidence

ORD record
ord-316fe55b69164094b10892019c99a8b3
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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