Dimethylformamide → HCID 11261333, compound

HRID 2221354Notes

Reaction equation

HRID 2221354 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)[CH3:2].[NH2:13][CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][C:25]([NH:27][CH:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:31][CH2:30][CH2:29]3)=[O:26])[CH:22]=2)[O:17][C:16]([CH3:39])([CH3:38])[CH:15]1[OH:40].C(N(CC)CC)C.CN(C)C=O>ClCCl.O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:13][CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][C:25]([NH:27][CH:28]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH2:31][CH2:30][CH2:29]4)=[O:26])[CH:22]=3)[O:17][C:16]([CH3:38])([CH3:39])[CH:15]2[OH:40])(=[O:11])=[O:10])=[CH:5][CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 5709594-Ethylbenzene-1-sulfonyl chlorideHCID 69061410HCID 69061410, compound

Product 1

HCID 11261333HCID 11261333, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.67 g 4-ethyl benzenesulfonyl chloride was added dropwise to a solution of 3.75 g of the 2-(4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-N-1,2,3,4-tetrahydronaphth-1-yl acetamide obtained above and 8.4 ml triethylamine in 160 ml dichloromethane. In addition 5 ml of dimethyl formamide (=DMF) was added, and the resulting mixture was stirred for 18 hours at room temperature. Then 100 ml water was added, and the mixture was stirred for another 5 minutes. The organic phase was separated, and the solvent was evaporated at reduced pressure. The remaining residue was chromatographed on silica gel (mobile phase: ethyl acetate/cyclohexane/methanol 110:140:2 v/v/v), and the product phases were combined and reduced in volume. The residue was stirred with petroleum ether/diethyl ether 10:1 v/v. The resulting crystals were removed by suction and dried on a rotary evaporator at 40° C. and 25 bar. 2.3 g of the title compound was obtained as colorless crystals.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for another 5 minutes
  3. customThe organic phase was separated
  4. customthe solvent was evaporated at reduced pressure
  5. customThe remaining residue was chromatographed on silica gel (mobile phase: ethyl acetate/cyclohexane/methanol 110:140:2 v/v/v)
  6. stirringThe residue was stirred with petroleum ether/diethyl ether 10:1 v/v
  7. customThe resulting crystals were removed by suction
  8. customdried on a rotary evaporator at 40° C.

Sources & evidence

ORD record
ord-cbcb270bf3d0450a84af29f1e15786bb
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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