Ammonium Chloride → HCID 59655000, compound

HRID 2053454Notes

Reaction equation

HRID 2053454 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br-].CSC.[CH2:13]([N:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[C:23](OS(C(F)(F)F)(=O)=O)=[C:22]([C:39]2[O:43][N:42]=[C:41]([CH3:44])[CH:40]=2)[C:21]1=[O:45])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH4+].[Cl-]>C1COCC1.O>[CH2:13]([N:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[C:23]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:22]([C:39]2[O:43][N:42]=[C:41]([CH3:44])[CH:40]=2)[C:21]1=[O:45])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 21888262HCID 21888262, compoundHCID 59654957HCID 59654957, compoundHCID 178478990HCID 178478990, compound

Product 1

HCID 59655000HCID 59655000, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of cyclohexylmagnesium chloride (250 ul, 0.50 mmol, 2M in THF) was added to a suspension of cupper (I) bromide-dimethylsulfide (51 mg, 0.25 mmol) in 2 ml of THF at −78° C. under N2. The mixture was warmed to rt until a dark color homogenous solution was observed (ca. 15 min), then re-cooled to −78° C. A solution of trifluoro-methanesulfonic acid 1-benzyl-6-chloro-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinolin-4-yl ester (80 mg, 0.16 mmol) in 2 ml of THF was added to the mixture. The resulting mixture was stirred at −78° C. for 2 h and warmed to rt. Treated with 2 ml of sat. NH4Cl followed by 20 ml H2O, the mixture was extracted with EtOAc (2×20 ml). The combined organic layers were washed with H2O (10 ml), brine (10 ml) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (20-30% EtOAc/hexanes) gave 61 mg (88%) of product as a white solid: 1H-NMR (CDCl3; 400 MHz) δ8.08 (br s, 1H), 7.40 (dd, 1H, J=9.2, 2.2 Hz), 7.20-7.34 (m, 6H), 6.42 (s, 1H), 5.53 (s, 2H), 2.98 (br s, 1H), 2.41 (s, 3H), 1.67-1.93 (m, 7H), 1.22-1.40 (m, 3H). Mass spectrum (ESI, m/z): Calcd. for C26H25ClN2O2, 433.2 (M+H), found 433.1.

Workup

  1. custom(ca. 15 min)
  2. temperaturere-cooled to −78° C
  3. temperaturewarmed to rt
  4. extractionthe mixture was extracted with EtOAc (2×20 ml)
  5. washThe combined organic layers were washed with H2O (10 ml), brine (10 ml)
  6. dry with materialdried (Na2SO4)
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-e8a8b5078bb04e79ba92891081788f2c
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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