1-Hydroxybenzotriazole → HCID 49848080, compound

HRID 340620Notes

Reaction equation

HRID 340620 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:8]=[C:9]([N:11]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[CH3:12])[CH:10]=1)=O.[N:25]1[CH:30]=[CH:29][N:28]=[CH:27][C:26]=1[CH:31]([NH2:33])[CH3:32].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[N:25]1[CH:30]=[CH:29][N:28]=[CH:27][C:26]=1[CH:31]([NH:33][C:3]([C:5]1[CH:6]=[C:7]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[CH:8]=[C:9]([N:11]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[CH3:12])[CH:10]=1)=[O:2])[CH3:32]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 185190061-(Pyrazin-2-yl)ethanamineHCID 596275315-(Isobutyryl-methyl-amino)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 49848080HCID 49848080, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Isobutyryl-methyl-amino)-4′-methyl-biphenyl-3-carboxylic acid methyl ester (67 mg, 0.22 mmol) was added to methylene chloride (3 mL) and stirred at room temperature. TEA (0.87 g), 1-pyrazin-2-yl-ethylamine (32 mg, 0.25 mmol), HOBt (29 mg) and ECDI (54 mg) were added, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was placed directly onto a silica column and eluted with 50% ethyl acetate/hexanes to give 32 mg of 5-(isobutyryl-methyl-amino)-4′-methyl-biphenyl-3-carboxylic acid (1-pyrazin-2-yl-ethyl)-amide as a white solid, MS (M+H)=417.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. washeluted with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-eae12d9697164ef7abd0174a41edec7c
Source dataset
uspto-grants-2014_11
Patent number
US08895589B2

Reaction notes

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