Water → HCID 23517371, compound

HRID 1835992Notes

Reaction equation

HRID 1835992 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][C:12]3[C:18]([C:19](O)=[O:20])=[CH:17][C:16]([O:22][CH3:23])=[CH:15][C:13]=3[CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[CH3:25][NH:26][O:27][CH3:28].CCN=C=NCCCN(C)C.O>CN(C1C=CN=CC=1)C.CN(C)C=O>[CH3:28][O:27][N:26]([CH3:25])[C:19]([C:18]1[C:12]2[O:11][C:10]([C:4]3[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=3)=[CH:14][C:13]=2[CH:15]=[C:16]([O:22][CH3:23])[CH:17]=1)=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 10286458HCID 10286458, compound

Product 1

HCID 23517371HCID 23517371, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 44 (0.400 g, 1.27 mmole), N,O dimethylhydroxylamine hydrochloride (0.247 g, 2.53 mmole), DMAP (0.309 g, 2.53 mmole), and EDCI (0.364 g, 1.90 mmole), in 40 mL dimethylformamide was stirred at rt for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 7:3) to afford 0.290 g (63%) of amide 45 as a tan solid: Mp=100-102° C.; 1H NMR (DMSO-d6) δ 7.74 (dd, 1H, J=2.0 Hz), 7.66 (d, 1 H, J=8.6 Hz), 7.37 (s, 1 H), 7.31 (t, 1 H, J=8.7 Hz), 7.24 (d, 1 H, J=2.6 Hz), 6.93 (d, 1 H, J=2.6 Hz), 3.90 (s, 3 H), 3.82 (s, 3 H), 3.59 (br s, 3 H), 3.30 (s, 3H); MS 360 (M+H)+

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe organic phases were concentrated
  5. customchromatographed with silica gel (hexanes:ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-050d8decb4854f20b7e5fada0a1c63a4
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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