Cyanamide → [4-Amino-2-[4-(2-ethylamino-ethoxy)-phenylamino]-thiazol-5-yl]-benzo[1,3]dioxol-5-yl-methanone

Reaction equation

[N:1]#[C:2][NH2:3].C(OC(=O)[N:10]([CH2:23][CH3:24])[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[S:22])=[CH:16][CH:15]=1)(C)(C)C.[O:26]1[C:30]2[CH:31]=[CH:32][C:33]([C:35](=[O:38])[CH2:36]Br)=[CH:34][C:29]=2[O:28][CH2:27]1>>[NH2:1][C:2]1[N:3]=[C:21]([NH:20][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][NH:10][CH2:23][CH3:24])=[CH:19][CH:18]=2)[S:22][C:36]=1[C:35]([C:33]1[CH:32]=[CH:31][C:30]2[O:26][CH2:27][O:28][C:29]=2[CH:34]=1)=[O:38]

Participants

Reactant 3

HCID 9864Cyanamide

HCID 2437771-(1,3-Dioxaindan-5-yl)-2-bromoethan-1-one

HCID 23525784Ethyl-[2-(4-isothiocyanato-phenoxy)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 10477555[4-Amino-2-[4-(2-ethylamino-ethoxy)-phenylamino]-thiazol-5-yl]-benzo[1,3]dioxol-5-yl-methanone

Procedure

This compound was prepared from cyanamide, ethyl-[2-(4-isothiocyanato-phenoxy)-ethyl]-carbamic acid tert-butyl ester of Example 129D and 1-benzo[1,3]dioxol-5-yl-2-bromoethanone (Example 132) following a procedure similar to Example 130. The crude product was purified by HPLC using a Waters Symmetry C-18 21.2×75 mm column with the following gradient: A (0.05% trifluoroacetic acid in water), B (0.035% trifluoroacetic acid in acetonitrile, A to B gradient (0 to 50% over 7 minutes) flow rate: 20 mL/minute. The recovered product was dissolved in ethyl acetate, washed with 0.05N aqueous sodium hydroxide, and then with water. The ethyl acetate was dried (Na2SO4), concentrated, and the resulting residue triturated with ether to yield the product. Mass spectrum (ES) MH+=427.