Tetrahydrofuran → HCID 178474352, compound

HRID 2243869Notes

Reaction equation

HRID 2243869 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:27][O:28][CH2:29][CH3:30])[CH2:12][C:13](=[O:26])[NH:14][C:15](=[N:18]C(=O)OC(C)(C)C)SC)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[NH2:31][CH2:32][C:33]1[CH:39]=[C:38]([Cl:40])[C:36]([NH2:37])=[C:35]([Cl:41])[CH:34]=1.[CH:42]([N:45]([CH:48](C)C)CC)(C)[CH3:43].C1C[O:54]CC1>>[CH2:29]([O:28][N:27]=[C:11]1[C:8]2[CH:7]=[CH:6][C:5](=[CH:10][CH:9]=2)[O:4][CH2:1][CH:2]=[CH:3][CH2:48][NH:45][CH2:42][C:43](=[O:54])[NH:37][C:36]2[C:35]([Cl:41])=[CH:34][C:33](=[CH:39][C:38]=2[Cl:40])[CH2:32][NH:31][C:15]([NH2:18])=[N:14][C:13](=[O:26])[CH2:12]1)[CH3:30]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 189757634-Amino-3,5-dichlorobenzylamineHCID 72531903tert-Butyl 7-(4-(allyloxy)phenyl)-5-oxo-9-oxa-2-thia-4,8-diazaundec-7-en-3-ylidenecarbamate

Product 1

HCID 178474352HCID 178474352, compound

Conditions

Temperature
58 °C

Procedure

A solution of tert-butyl 7-(4-(allyloxy)phenyl)-5-oxo-9-oxa-2-thia-4,8-diazaundec-7-en-3-ylidenecarbamate from Step D (1.14 g) in THF (4 mL) was added 4-(aminomethyl)-2,6-dichloroaniline (647 mg) and diisopropylethylamine (0.46 mL), and the resulting mixture was heated at 58° C. for 12 h. The solvents were removed in vacuo, and the residue was purified by Biotage eluting with 10-25% ethyl acetate/90-75% hexanes to give the title compound as a yellowish oil (1.28 g). retention time: 2.37 min (method A). MS (ESI) (M+H)+ 578.23.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by Biotage
  3. washeluting with 10-25% ethyl acetate/90-75% hexanes

Sources & evidence

ORD record
ord-9948d7209db54573a003fb4b488fe3c3
Source dataset
uspto-grants-2010_03
Patent number
US07678784B2

Reaction notes

Loading…