1,2-Dichloroethane → N-[(3-Chloro-pyrazin-2-yl)-(4-phenoxy-phenyl)-methyl]-formamide

HRID 449038Notes

Reaction equation

HRID 449038 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:15][C:16]1[C:17]([CH:22]([NH2:36])[C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[N:18][CH:19]=[CH:20][N:21]=1.CCN(C(C)C)C(C)C.C[CH2:47][O:48]C(C)=O.C(Cl)Cl>C(Cl)Cl.C(O)=O>[Cl:15][C:16]1[C:17]([CH:22]([C:23]2[CH:24]=[CH:25][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:27][CH:28]=2)[NH:36][CH:47]=[O:48])=[N:18][CH:19]=[CH:20][N:21]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 21226138Dichloromethane ethylacetateHCID 59341168HCID 59341168, compound

Product 1

HCID 86636036N-[(3-Chloro-pyrazin-2-yl)-(4-phenoxy-phenyl)-methyl]-formamide

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of formic acid. (0.38 mL, 9.6 mmol), EDC (1.84 g, 9.6 mmol) and HOBt (0.2 g, 1.3 mmol) in CH2Cl2 (25 mL) under nitrogen were added compound C-(3-chloropyrazin-2-yl)-C-(4-phenoxyphenyl)-methylamine (2.0 g, 6.4 mmol), followed by DIEA (2.2 mL, 12.8 mmol). The mixture was stirred for 16 h at rt. TLC (EtOAc/CH2Cl2, 1:1) showed no starting material. The reaction mixture was diluted with CH2Cl2 (75 mL), washed with water (3×50 mL) and dried (Na2SO4). Evaporation of solvent gave desired product, which was used for next step without any further purification. Yield: 1.85 g (84%). 1H NMR (CDCl3, 300 MHz) δ 6.61 (d, J=6.8 Hz, 1H), 6.70-6.99 (m, 4H), 7.16 (t, J=7.2 Hz, 1H), 7.27-7.32 (m, 4H), 8.29 (s, 1H), 8.38 (d, J=2.4 Hz, 1H), 8.61 (d, J=2.4 Hz, 1H).

Workup

  1. washwashed with water (3×50 mL)
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of solvent

Sources & evidence

ORD record
ord-3440ab5b7abf4137ab5a5ff9718c77d4
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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