Dimethylamine, hydrochloride → (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(dimethylcarbamoyl)-7-methylquinolin-6-yl)acetate

HRID 931770Notes

Reaction equation

HRID 931770 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[N:18]=[C:17]([C:23]([OH:25])=O)[CH:16]=[CH:15]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:34][NH:35][CH3:36].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[N:18]=[C:17]([C:23](=[O:25])[N:35]([CH3:36])[CH3:34])[CH:16]=[CH:15]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66631131(S)-6-(1-tert-Butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-7-methylquinoline-2-carboxylic acid

Product 1

HCID 68595355(S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(dimethylcarbamoyl)-7-methylquinolin-6-yl)acetateYield 45.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-7-methylquinoline-2-carboxylic acid (14 mg, 0.032 mmol), dimethylamine HCl salt (13 mg, 0.16 mmol) and DIPEA (0.056 mL, 0.32 mmol) in DMF (1 mL) was added HATU (61 mg, 0.16 mmol) at 0° C. The mixture was stirred for 2 hours at ambient temperature. The mixture was diluted with ethyl acetate (30 mL) and washed with water and brine, then dried over Na2SO4. Concentration and purification by column chromatography provided the product (7 mg, 45%). LCMS-ESI+ (m/z): 483.2, 485.3 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration and purification by column chromatography

Sources & evidence

ORD record
ord-bae2da151f944774b86f7487a3c84090
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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