1,2-Dichloroethane → HCID 59710989, compound

HRID 2221464Notes

Reaction equation

HRID 2221464 reaction equation
[NH2:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][C:24]([C:26]1[C:27]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:25])[CH:17]=[CH:16]2)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:42](O)(=[O:45])[CH2:43][CH3:44].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.C(N(CC)CC)C>[C:4]1([C@H:3]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[C:18]([NH:23][C:24]([C:26]2[C:27]([C:32]4[CH:33]=[CH:34][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:36][CH:37]=4)=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:25])[CH:17]=[CH:16]3)=[O:12])[CH2:2][NH:1][C:42](=[O:45])[CH2:43][CH3:44])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1032Propionic AcidHCID 757711-HydroxybenzotriazoleHCID 59710981HCID 59710981, compound

Product 1

HCID 59710989HCID 59710989, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

(S)-2-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-6-carboxylic acid (2-amino-1-phenyl-ethyl)-amide (N, 30 mg, 0.05 mM), proprionic acid (0.075 mM), EDC (14 mg, 0.075 mM), HOBT (11 mg, 0.075 mM), and triethylamine (0.03 mL, 0.21 mM) were taken up in CH2Cl2 (1 mL) and stirred at room temperature for 16 h. The mixture was concentrated and the residue was purified by flash chromatography (silica gel) eluting with EtOAc/hexanes. HPLC retention time, 2.87 min; ESMS (m+1), 611; calc. Mw, 610

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography (silica gel)
  3. washeluting with EtOAc/hexanes
  4. customHPLC retention time, 2.87 min

Sources & evidence

ORD record
ord-8e26bb651d114f669a93f9bb3bbb366a
Source dataset
uspto-grants-2008_05
Patent number
US07368573B2

Reaction notes

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