3-Bromoaniline → HCID 19062908, compound

HRID 2172672Notes

Reaction equation

HRID 2172672 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[N:18]1([CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Br:10][C:11]1[CH:12]=[C:13]([NH:17][C:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:25]([CH2:24][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:26][CH:27]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 115623-BromoanilineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10929754-(piperidin-1-ylmethyl)benzoic acid

Product 1

HCID 19062908HCID 19062908, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (433 μL, 2.49 mmol) was added into a suspension of 3-bromobenzenamine (90.3 μL, 0.829 mmol), 4-(piperidin-1-ylmethyl)benzoic acid (200 mg, 0.912 mmol), BOP (477 mg, 1.08 mmol) in DMF (2 mL). The reaction mixture was stirred at room temperature under argon atmosphere overnight. The reaction mixture was loaded onto a 5 g silica loading cartridge. After solvent in the cartridge was dried out under vacuum, the cartridge was put on the ICSO system for purification (yield: 80%). MS (ESI+) m/z 373.0 [M+H]+.

Workup

  1. customAfter solvent in the cartridge was dried out under vacuum
  2. customthe cartridge was put on the ICSO system for purification (yield: 80%)

Sources & evidence

ORD record
ord-99548ff6e5784f9f9e70d93ab22312a1
Source dataset
uspto-grants-2015_06
Patent number
US09056837B2

Reaction notes

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