Diisopropylethylamine → HCID 90312468, compound

HRID 1505823Notes

Reaction equation

HRID 1505823 reaction equation
[CH3:1][O:2][CH:3]([O:21][CH3:22])[CH2:4][N:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:15][CH3:16])[C:8](=[O:17])[C:7]([C:18]([OH:20])=O)=[CH:6]1.C(N(CC)C(C)C)(C)C.[F:32][C:33]1[CH:38]=[CH:37][C:36]([C@H:39]([NH2:41])[CH3:40])=[CH:35][CH:34]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[CH3:22][O:21][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[CH:6]=[C:7]([C:18](=[O:20])[NH:41][C@@H:39]([C:36]2[CH:37]=[CH:38][C:33]([F:32])=[CH:34][CH:35]=2)[CH3:40])[C:8](=[O:17])[C:9]([O:15][CH3:16])=[C:10]1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6950187(1R)-(+)-1-(4-Fluorophenyl)ethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534690001-(2,2-diMethoxyethyl)-5-Methoxy-6-(Methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 90312468HCID 90312468, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2,2-dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (1-A, 0.500 g, 1.59 mmol), was suspended in acetonitrile (6 mL) and treated with N,N-diisopropylethylamine (DIPEA) (0.550 mL, 3.17 mmol), (R)-1-(4-fluorophenyl)ethanamine (0.242 mg, 1.74 mmol) and HATU (0.661 g, 1.74 mmol). The reaction mixture was stirred for 2 hours and partitioned between ethyl acetate and water. The organic layer was separated and washed with HCl (10% aq), sodium bicarbonate (1M aq), dried over sodium sulfate, filtered and concentrated to afford crude (R)-methyl 1-(2,2-dimethoxyethyl)-5-(1-(4-fluorophenyl)ethylcarbamoyl)-3-methoxy-4-oxo-1,4-dihydropyridine-2-carboxylate which was used without purification in the next step: LCMS-ESI+ (m/z): [M+H]+ calculated for C21H26FN2O2: 437.17; found: 437.1.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with HCl (10% aq), sodium bicarbonate (1M aq)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9598ecb4c4414528b18c353bc5bea5c3
Source dataset
uspto-grants-2015_12
Patent number
US09216996B2

Reaction notes

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