Dimethylamine → (4R)-1-(5-chloro-3-{5-[2-(dimethylamino)ethyl]-2-methoxyphenyl}-1-{[4-methoxy-2-(trifluoro methoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-L-prolin amide

HRID 1662757Notes

Reaction equation

HRID 1662757 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][C:23]([F:26])([F:25])[F:24])(=[O:13])=[O:12])[C:6](=[O:27])[C:5]2([N:39]1[CH2:48][C@H:47]([OH:49])[CH2:46][C@H:40]1[C:41]([N:43]([CH3:45])[CH3:44])=[O:42])[C:28]1[CH:33]=[C:32]([CH2:34][CH:35]=O)[CH:31]=[CH:30][C:29]=1[O:37][CH3:38].[CH3:50][NH:51][CH3:52].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][C:23]([F:24])([F:25])[F:26])(=[O:12])=[O:13])[C:6](=[O:27])[C:5]2([N:39]1[CH2:48][C@H:47]([OH:49])[CH2:46][C@H:40]1[C:41]([N:43]([CH3:45])[CH3:44])=[O:42])[C:28]1[CH:33]=[C:32]([CH2:34][CH2:35][N:51]([CH3:52])[CH3:50])[CH:31]=[CH:30][C:29]=1[O:37][CH3:38]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59867806HCID 59867806, compound

Product 1

HCID 59867773(4R)-1-(5-chloro-3-{5-[2-(dimethylamino)ethyl]-2-methoxyphenyl}-1-{[4-methoxy-2-(trifluoro methoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-L-prolin amide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of 150 mg of the compound obtained in Example 218, a solution of 2 mol/L dimethylamine in THF (0.22 ml), 63 mg of acetic acid, 95 mg of sodium triacetoxy borohydride, in CHCl3 (1.5 ml) was stirred at room temperature for one hour. A saturated aqueous solution of NaHCO3 was added to the reaction solution, and the resulting mixture was extracted with CHCl3. The extract was dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. Purification was carried out by a preparative TLC plate (1 mm; mobile phase: CHCl3/MeOH=8/1; v/v) to obtain 75 mg of the title compound (colorless solid).

Workup

  1. extractionthe resulting mixture was extracted with CHCl3
  2. dry with materialThe extract was dried over Na2SO4
  3. customthe drying agent was separated by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-d41da3e3cac54c9b8ebff1fc80a4f658
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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