Methyl chloroformate → {4-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-carbamic acid methyl ester

HRID 859050Notes

Reaction equation

HRID 859050 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]3[C:21]4[N:22]=[C:23]([NH2:25])[S:24][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH:10]=2)=[CH:5][CH:4]=1.Cl[C:29]([O:31][CH3:32])=[O:30]>N1C=CC=CC=1.CCOC(C)=O>[CH3:32][O:31][C:29](=[O:30])[NH:25][C:23]1[S:24][C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:15][C:11]3[CH:10]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:26])([F:1])[F:27])=[CH:4][CH:5]=4)[N:14]=[CH:13][N:12]=3)[C:21]=2[N:22]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 100916504-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine

Product 1

HCID 58759715{4-[6-(4-Trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-carbamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-ylamine, (Example 65) (100 mg, 0.26 mmol) in pyridine (2 mL) was added methyl chloroformate (28 mg, 0.29 mmol, Aldrich) at 0° C. The reaction mixture was stirred at room temperature for 2 h, diluted with EtOAc and washed with 1 N NaOH and water. The EtOAc layer was separated, dried over Na2SO4, filtered and evaporated in vacuum. Purification of the residue by silica gel chromatography with gradient: 40 to 80% EtOAc in hexanes gave the title compound as an off white solid. MS (ESI, pos. ion.) m/z: 447 (M+1).

Workup

  1. washwashed with 1 N NaOH and water
  2. customThe EtOAc layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuum
  6. customPurification of the residue by silica gel chromatography with gradient

Sources & evidence

ORD record
ord-3c364f87bbc8470fa88659a447dc31e6
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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