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
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.
Workup
- customThe crude product was purified by HPLC
- customto B gradient (0 to 50% over 7 minutes) flow rate: 20 mL/minute
- dissolutionThe recovered product was dissolved in ethyl acetate
- washwashed with 0.05N aqueous sodium hydroxide
- dry with materialThe ethyl acetate was dried (Na2SO4)
- concentrationconcentrated
- customthe resulting residue triturated with ether
- customto yield the product
Sources & evidence
- ORD record
- ord-7116cd9769444783a67edad070152096
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06818663B2
Reaction notes
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