Triethylamine → 6-(2-Amino-pyrimidin-4-yloxy)-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

HRID 556353Notes

Reaction equation

HRID 556353 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([O:20][C:21]4[CH:26]=[C:25](Cl)[N:24]=[C:23]([NH2:28])[N:22]=4)=[CH:19][C:14]=3[S:13][N:12]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].CCN(CC)CC>C1COCC1.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([O:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([NH2:28])[N:22]=4)=[CH:19][C:14]=3[S:13][N:12]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:30])[F:31]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 866266256-(2-Amino-6-chloro-pyrimidin-4-yloxy)-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

Product 1

HCID 247627056-(2-Amino-pyrimidin-4-yloxy)-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenation of 51 mg (0.11 mMol) of 6-(2-amino-6-chloro-pyrimidin-4-yloxy)-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide (Step 6.3) in 10 ml THF and 46 μl (0.33 mMol) Et3N in presence of two portions of 0.1 g Pd/C (10%; Engelhard 4505) during 36 h, filtration, concentration of the filtrate and chromatography (Combi Flash; CH2Cl2/hexane 2:3→CH2Cl2→CH2Cl2/ether 7:3) gives the title compound: m.p.: 237-239° C.; MS: [M+1]+=450.

Workup

  1. filtrationfiltration, concentration of the filtrate and chromatography (Combi Flash; CH2Cl2/hexane 2:3→CH2Cl2→CH2Cl2/ether 7:3)

Sources & evidence

ORD record
ord-150ef210b19b465e931062c7d79c8a7f
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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