Dimethylamine → HCID 178464137, compound

HRID 1170436Notes

Reaction equation

HRID 1170436 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1([OH:37])[C:18]2[C:13](=[CH:14][C:15]([C:23]([OH:25])=O)=[CH:16][C:17]=2[C:19]([F:22])([F:21])[F:20])[N:12]([CH2:26][C@H:27]2[CH2:30][C@H:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[CH2:28]2)[C:11]1=[O:36].[CH3:38][NH:39][CH3:40].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C=O>[ClH:2].[CH3:38][N:39]([CH3:40])[C:23]([C:15]1[CH:14]=[C:13]2[C:18]([C:10]([C:4]3[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:3]=3[Cl:2])([OH:37])[C:11](=[O:36])[N:12]2[CH2:26][C@H:27]2[CH2:30][C@H:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[CH2:28]2)=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=1)=[O:25]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 516892Sodium BicarbonateHCID 178419562HCID 178419562, compound

Product 1

HCID 178464137HCID 178464137, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 8 (200 mg, 0.32 mmol) in dichloromethane (5 mL) and N,N-dimethylformamide (5 mL) were added excess amount of dimethylamine and bis-(2-oxo-3-oxazolidinyl)-phosphinic chloride (325.2 mg, 1.27 mmol), and the mixture was stirred at room temperature for 28 hours. To the reaction solution was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate-toluene (1:1). The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol/ammonia water=20/1/0 to 10/1/0 to 200/10/1 to 100/10/1). To the purified substance were added tetrahydrofuran and 1M hydrochloric acid (1 mL), and the mixture was concentrated. The resulting solid was suspended in diethyl ether, and then filtered to give the titled compound (139.0 mg, 72%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate-toluene (1:1)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol/ammonia water=20/1/0 to 10/1/0 to 200/10/1 to 100/10/1)
  6. additionTo the purified substance were added tetrahydrofuran and 1M hydrochloric acid (1 mL)
  7. concentrationthe mixture was concentrated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-40a32d686c334b3c98c8d9b43b1c679d
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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