Cyanamide → HCID 23525780, compound

HRID 2415298Notes

Reaction equation

HRID 2415298 reaction equation
[N:1]#[C:2][NH2:3].[C:4]([O:8][C:9](=[O:26])[N:10]([CH2:24][CH3:25])[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[CH2:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([F:45])[CH:38]=1)=[O:36]>C(#N)C.C(O)(C)(C)C.O>[C:4]([O:8][C:9](=[O:26])[N: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:34]([C:35](=[O:36])[C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([F:45])[CH:38]=3)=[C:2]([NH2:3])[N:1]=2)=[CH:19][CH:20]=1)[CH2:24][CH3:25])([CH3:6])([CH3:7])[CH3:5]

Participants

8

Reactant 4

HCID 9864CyanamideHCID 70618463-Fluoro-4-methoxyphenacyl bromideHCID 23665647Potassium tert-butoxideHCID 86590647HCID 86590647, compound

Product 1

HCID 23525780HCID 23525780, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of cyanamide (21.2 mg, 0.499 mmol) (Aldrich) in acetonitrile (2.5 mL) and tert-butanol (2.5 mL) was added ethyl-[3-(4-isothiocyanato-phenoxy)propyl]carbamic acid tert-butyl ester (153.8 mg, 0.4571 mmol from Example 66, step C) followed by a solution of potassium tert-butoxide (0.50 mL, 1 M in tert-butanol) (Aldrich). After 30 minutes at room temperature, 2-bromo-1-(3-fluoro-4-methoxyphenyl)ethan-1-one (112.5 mg, 0.4553 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)-ethyl-carbamic acid tert-butyl ester (245.1.6 mg, 99% yield). HRMS, observed: 545.2230; Calcd for M+H: 545.2229.

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-a27a497a4a4a42fc8d7519d253c67fc5
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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