Cyanamide → [4-Amino-2-[4-(2-ethylamino-ethoxy)-phenylamino]-thiazol-5-yl]-(3-methoxy-phenyl)-methanone

HRID 2415280Notes

Reaction equation

HRID 2415280 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.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1)=[O:29]>>[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:27]=1[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1)=[O:29]

Participants

4

Reactant 3

HCID 9864CyanamideHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 23525784Ethyl-[2-(4-isothiocyanato-phenoxy)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 9979067[4-Amino-2-[4-(2-ethylamino-ethoxy)-phenylamino]-thiazol-5-yl]-(3-methoxy-phenyl)-methanone

Procedure

This compound was prepared from cyanamide, ethyl-[2-(4-isothiocyanato-phenoxy)-ethyl]-carbamic acid tert-butyl ester of Example 129D and 2-bromo-1-(3-methoxyphenyl)ethanone (Aldrich) following the procedure of Example 123. The protecting group was removed with 50% trifluoroacetic acid in dichloromethane, evaporated to a gum, taken into ethyl acetate, treated with 0.01N aqueous sodium hydroxide for 15 minutes and then washed with water. The ethyl acetate was dried (Na2SO4) and concentrated to a semi-solid which was triturated with ether to yield solid [4-amino-2-[4-(2-ethylamino-ethoxy)-phenylamino]-thiazol-5-yl]-(3-methoxy-phenyl)-methanone. Mass spectrum (ES) MH+=413.

Workup

  1. customThe protecting group was removed with 50% trifluoroacetic acid in dichloromethane
  2. customevaporated to a gum
  3. additiontreated with 0.01N aqueous sodium hydroxide for 15 minutes
  4. washwashed with water
  5. dry with materialThe ethyl acetate was dried (Na2SO4)
  6. concentrationconcentrated to a semi-solid which
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-d354da8f5e9c48ab8c06ca67fda70918
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

Loading…