Water → HCID 58707330, compound

HRID 1910606Notes

Reaction equation

HRID 1910606 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][CH:6]2[NH2:13].F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[S:22]([CH3:25])(=[O:24])=[O:23].C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][CH:6]2[NH:13][C:17]1[CH:18]=[C:19]([F:21])[CH:20]=[CH:15][C:16]=1[S:22]([CH3:25])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzeneHCID 529888476-Chloro-3,4-dihydro-2H-1-benzopyran-4-amine--hydrogen chloride (1/1)

Product 1

HCID 58707330HCID 58707330, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-chlorochroman-4-amine hydrochloride (551.0 mg, 2.50 mmol), 2,4-difluoro-1-(methylsulfonyl)benzene (496.0 mg, 2.50 mmol) and diisopropylethylamine (1.29 g, 10.0 mmol) in N,N-dimethylformamide (10 mL) was stirred at 110° C. for 16 h. The reaction was cooled to room temperature, poured over water and extracted with diethyl ether. The solvent was concentrated in vacuo and the residue was purified by silica chromatography (20% ethyl acetate in hexanes) to yield 143.0 mg (16%) of the desired product: 1H NMR (400 MHz, CDCl3) δ 7.82 (dd, 1H), 7.19 (m, 2H), 6.83 (d, 1H), 6.57 (m, 2H), 4.60 (m, 1H), 4.30 (m, 1H), 4.28 (m, 1H), 3.01 (s, 3H), 2.19 (m, 2H).

Workup

  1. extractionextracted with diethyl ether
  2. concentrationThe solvent was concentrated in vacuo
  3. customthe residue was purified by silica chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7011fcd3292c4e048968c3997cb3e403
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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