4-Amino-4'-chlorodiphenyl → HCID 71060069, compound

HRID 405271Notes

Reaction equation

HRID 405271 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[C:14]([OH:16])=O.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[Br:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[C:14]([NH:34][C:31]1[CH:30]=[CH:29][C:28]([C:25]2[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=2)=[CH:33][CH:32]=1)=[O:16]

Participants

7

Reactant 5

HCID 86754-Amino-4'-chlorodiphenylHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 331283-Bromo-5-chlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 71060069HCID 71060069, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat i-Pr2NEt (0.21 mL, 1.19 mmol) was added to a DCM mixture (5 mL) of 3-bromo-5-chlorobenzoic acid (140 mg, 0.60 mmol), 4′-chloro-[1,1′-biphenyl]-4-amine (145 mg, 0.71 mmol), HOBt (92 mg, 0.60 mmol) and EDCI (114 mg, 0.60 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting precipitate was filtered off, washed with water and MeOH, and dried in vacuo to yield the title compound.

Workup

  1. filtrationAfter 16 h the resulting precipitate was filtered off
  2. washwashed with water and MeOH
  3. customdried in vacuo

Sources & evidence

ORD record
ord-bf95869ebfbf4da680ba2bf9544dbcb8
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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