1,2-Dichloroethane → HCID 18783797, compound

HRID 1108662Notes

Reaction equation

HRID 1108662 reaction equation
C(Cl)CCl.Cl.[N:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[C:19]([OH:22])(=[O:21])[CH3:20].C(OC([N:30]1[CH2:35][CH2:34][CH:33]([C:36](O)=[O:37])[CH2:32][CH2:31]1)=O)(C)(C)C.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C>CN(C=O)C>[N:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:18]=[CH:17][C:15]([NH:16][C:36]([CH:33]3[CH2:34][CH2:35][N:30]([CH2:20][C:19]([OH:22])=[O:21])[CH2:31][CH2:32]3)=[O:37])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 18783776HCID 18783776, compoundHCID 70072880HCID 70072880, compound

Product 1

HCID 18783797HCID 18783797, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (316.3 mg, 1.65 mmol) was added to a solution 4-(4-pyridinyl)aniline hydrochloride 34 (342 mg, 1.65 mmol), t-butoxycarbonyl-4-carboxypiperidine acetate 12 (365 mg, 1.5 mmol), HOBt.H2O (223 mg, 1.65 mmol) and DIEA (634 μmL, 3.64 mmol) in anhydrous DMF (10 mL) at RT. After stirring for 20 h, the reaction was concentrated on rotavap (high vacuum). The resulting residue was taken into EtOAc and washed successively with H2O (3×20 mL), 10% NaHCO3 (2×20 ml) and saturated NaCl. The organic extract was dried (anhydrous Na2SO4), filtered and concentrated to yield the title compound (500 mg, 84%) as a yellow solid. HPLC k' 6.35 (Ultrasphere® ODS, gradient, A:acetonitrile B:water-0.1% trifluoroacetic acid, 5-60% acetonitrile during 20 min; UV detection at 220 nm). MS (ESI) m/e 396.2[M+H]+.

Workup

  1. customat RT
  2. concentrationthe reaction was concentrated on rotavap (high vacuum)
  3. washwashed successively with H2O (3×20 mL), 10% NaHCO3 (2×20 ml) and saturated NaCl
  4. extractionThe organic extract
  5. dry with materialwas dried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d9dbe6070fd44f6db05178892dcd463f
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

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