Cyanamide → HCID 23525779, compound

HRID 2415296Notes

Reaction equation

HRID 2415296 reaction equation
[N:1]#[C:2][NH2:3].[C:4]([O:8][C:9](=[O:24])[NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[S:23])=[CH:17][CH:16]=1)([CH3:7])([CH3:6])[CH3:5].CC(C)([O-])C.[K+].Br[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([F:43])[CH:36]=1)=[O:34]>C(#N)C.C(O)(C)(C)C.O>[C:4]([O:8][C:9](=[O:24])[NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]2[S:23][C:32]([C:33](=[O:34])[C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([F:43])[CH:36]=3)=[C:2]([NH2:3])[N:1]=2)=[CH:19][CH:20]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

8

Reactant 4

HCID 9864CyanamideHCID 70618463-Fluoro-4-methoxyphenacyl bromideHCID 23665647Potassium tert-butoxideHCID 86590646HCID 86590646, compound

Product 1

HCID 23525779HCID 23525779, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of cyanamide (23.2 mg, 0.546 mmol) (Aldrich) in acetonitrile (2.5 mL) and tert-butanol (2.5 mL) was added [3-(4-Isothiocyanatophenoxy)-propyl]carbamic acid tert-butyl ester (from Example 64; 156.9 mg, 0.508 mmol) followed by a solution of potassium tert-butoxide (0.56 mL, 1 M in tert-BUOH). After 30 minutes at room temperature, 2-bromo-1-(3-fluoro-4-methoxy-phenyl)ethan-1-one (125.8 mg, 0.509 mmol) (Maybridge Chemical) was added. The reaction mixture was stirred at room temperature for 1 hour and then heated at 75° C. for 2 hours. The resulting mixture was poured into water (10 mL). The product was collected by filtration, washed with diethyl ether and dried in vacuo to provide (3-[4-[4-Amino-5-(3-fluoro-4-methoxy-benzoyl)-thiazol-2-ylamino]-phenoxy]-propyl)-carbamic acid tert-butyl ester (260.1 mg, 99% yield). HRMS, Observed: 517.1921; Calcd for M+H+:517.1916.

Workup

  1. temperatureheated at 75° C. for 2 hours
  2. filtrationThe product was collected by filtration
  3. washwashed with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-76d9a10b2d464149862860fc259d117a
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

Loading…