1,2-Dichloroethane → HCID 59710974, compound

HRID 2221463Notes

Reaction equation

HRID 2221463 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([NH:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:28](O)=[O:29])[CH:24]=4)[N:19]=3)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.Cl.[N:34]([CH2:37][C@@H:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[N+:35]=[N-:36].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCOC(C)=O.C(N(CC)CC)C>[N:34]([CH2:37][C@@H:38]([NH:45][C:28]([C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:17][C:15]([C:10]1[C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:31])([F:1])[F:32])=[CH:4][CH:5]=3)=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:16])[CH:27]=[CH:26]2)=[O:29])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[N+:35]=[N-:36]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 597109732-[[[4′-(Trifluoromethyl)[1,1′-biphenyl]-2-yl]carbonyl]amino]-6-quinolinecarboxylic acidHCID 131726860HCID 131726860, compound

Product 1

HCID 59710974HCID 59710974, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-6-carboxylic acid, (F-1a2, 0.78 g, 1.79 mM), (S)-2-azido-1-phenyl-ethylamine hydrochloride (0.36 g, 1.79 mM), EDC (0.41 g, 2.15 mM) and HOBT (10 mg, 0.075 mM), were dissolved in CH2Cl2 (15 mL) and treated with triethylamine (0.75 mL, 5.4 mM). The mixture was stirred at room temperature for 16 h, then was diluted with EtOAc (75 mL) and washed with 0.5 N HCl (20 mL), aqueous NaHCO3 (20 mL), and brine. The EtOAc fraction was dried (MgSO4), filtered and concentrated. ESMS (m+1), 581; calc. Mw, 580.

Workup

  1. washwashed with 0.5 N HCl (20 mL), aqueous NaHCO3 (20 mL), and brine
  2. dry with materialThe EtOAc fraction was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0e7bbd9c392a4f848aecb937baa19981
Source dataset
uspto-grants-2008_05
Patent number
US07368573B2

Reaction notes

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