Triethylamine → HCID 42601893, compound

HRID 404775Notes

Reaction equation

HRID 404775 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=3)[CH:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.Cl[CH2:32][CH2:33][S:34](Cl)(=[O:36])=[O:35]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:18]=[C:19]([NH:23][S:34]([CH:33]=[CH2:32])(=[O:36])=[O:35])[CH:20]=[CH:21][CH:22]=3)[CH:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 57708331HCID 57708331, compound

Product 1

HCID 42601893HCID 42601893, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[6-(3-chloro-4-fluorophenylamino)-pyrimidin-4-ylamino]phenylamine (IR-4) (300 mg, 0.9 mmol) and triethylamine (500 mg, 5 mmol) in 10 mL of THF was stirred at RT. 2-Chloroethanesulfonyl chloride (360 mg, 2.25 mmol) was added into the reaction mixture and stirring was continued at RT for 1 hr. The crude product was purified by flash chromatography on silica gel with EtOAc/heptane solvent system to afford 35 mg (9%) of the title compound, a brown colored solid. MS (m/z): MH+=420, 422. 1H NMR (DMSO): 9.92 (s, 1H), 9.29 (s, 1H), 9.21 (s, 1H), 8.26 (s, 1H), 7.92 (m, 1H), 7.40-7.22 (m, 4H), 7.14 (m, 1H), 6.20 (m, 2H), 6.05 (m, 3H) ppm.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel with EtOAc/heptane solvent system

Sources & evidence

ORD record
ord-8e4e04d71abd4880861e6797d764abe4
Source dataset
uspto-grants-2014_06
Patent number
US08748606B2

Reaction notes

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