1,2-Dichloroethane → HCID 52932106, compound

HRID 877372Notes

Reaction equation

HRID 877372 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:7].[CH:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](O)=[O:25])=[CH:19][CH:18]=1)([CH3:16])[CH3:15].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:7][C:24](=[O:25])[CH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH:14]([CH3:15])[CH3:16])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 782304-Isopropylphenylacetic acidHCID 181649HOAtHCID 67166773HCID 67166773, compound

Product 1

HCID 52932106HCID 52932106, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude 1-(1,3-oxazol-2-yl)-1-phenylmethanamine (0.10 g, 0.57 mmol) was mixed with 4-isopropylpheylacetic acid (0.10 g, 0.57 mmol), HOAt (0.086 g, 0.63 mmol) and EDC (0.12 g, 0.63 mmol) in DMF (1.0 mL) and stirred at room temperature for 0.5 h. Purification by reverse-phase HPLC gave the product (0.025 g, 13%). ES-MS [M+1]+: 335.1. 1H NMR (CDCl3, 400 MHz) δ 7.58 (s, 1H), 7.31-7.28 (m, 3H), 7.22-7.20 (m, 6H), 7.07 (s, 1H), 6.73 (d, J=8.0 Hz, 1H), 6.32 (d, J=7.6 Hz, 1H), 3.62 (s, 2H), 2.90 (m, J=6.8 Hz, 1H), 1.24 (d, J=6.8 Hz, 6H).

Workup

  1. customPurification by reverse-phase HPLC

Sources & evidence

ORD record
ord-b89ac02037014bbd8271c6458c2e8e4a
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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