1,2-Dichloroethane → 3-[(4-Fluoro-3-methylphenoxy)methyl]-1-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]azepane

HRID 467474Notes

Reaction equation

HRID 467474 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][C:3]=1[CH3:17].[N:18]1[N:19]([C:23]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:24]=2[C:25](O)=[O:26])[N:20]=[CH:21][CH:22]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:25](=[O:26])[C:24]3[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:23]=3[N:19]3[N:20]=[CH:21][CH:22]=[N:18]3)[CH2:9]2)=[CH:4][C:3]=1[CH3:17]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acidHCID 584052783-[(4-Fluoro-3-methylphenoxy)methyl]azepane

Product 1

HCID 461991443-[(4-Fluoro-3-methylphenoxy)methyl]-1-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]azepane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-6 (164 mg, 0.691 mmol) in DMF (4 ml) was treated with 1-7 (154 mg, 0.760 mmol), EDC (159 mg, 0.829 mmol), HOBT (127 mg, 0.829 mmol), and TEA (0.289 ml, 2.073 mmol). After stirring at RT for 30 min, the mixture was diluted with EtOAc, washed with water (3×s) and once with brine. The organic phase was dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica gel (0 to 100% EtOAc in Hex) to yield 1-8 as a pale yellow oil. Data for 1-8: LRMS m/z (M+H): 423.1.

Workup

  1. washwashed with water (3×s) and once with brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by gradient elution on silica gel (0 to 100% EtOAc in Hex)

Sources & evidence

ORD record
ord-b67fdae66f694a81829fb8bb4afd3ecc
Source dataset
uspto-grants-2014_01
Patent number
US08623863B2

Reaction notes

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