Chloroacetamide → HCID 25261978, compound

HRID 1894393Notes

Reaction equation

HRID 1894393 reaction equation
[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:39][CH2:38][C:37]4([CH2:44][CH2:43][NH:42][CH2:41][CH2:40]4)[CH2:36][CH2:35]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:45][CH2:46][CH3:47])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:49][C:50]([NH2:52])=[O:51]>C(N(CC)CC)C.CN(C)C=O.O>[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:35][CH2:36][C:37]4([CH2:44][CH2:43][N:42]([CH2:49][C:50]([NH2:52])=[O:51])[CH2:41][CH2:40]4)[CH2:38][CH2:39]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)([CH3:16])[N:15]=2)=[C:7]([O:45][CH2:46][CH3:47])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 6580ChloroacetamideHCID 25261826HCID 25261826, compound

Product 1

HCID 25261978HCID 25261978, compoundYield 91.7%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

The mixture of [(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-(3,9-diaza-spiro[5.5]undec-3-yl)-methanone (25 mg, 0.037 mmol, example 75), 2-chloroacetamide (6.9 mg, 0.074 mmol, Aldrich) and triethylamine (1 drop) in dimethylformamide (1 mL) was heated at 160° C. for 10 min using the microwave synthesizer. The mixture was diluted with water, extracted with ethyl ether (2×). The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated. The crude was filtered through a plug of silica gel, eluting with 5% methanol-ethyl acetate to give the title product as white solids (24.9 mg). HR-MS (ES, m/z) calculated for C40H51Cl2N6O3 [(M+H)+] 733.3394, observed 733.3392.

Workup

  1. extractionextracted with ethyl ether (2×)
  2. washThe extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. filtrationThe crude was filtered through a plug of silica gel
  6. washeluting with 5% methanol-ethyl acetate

Sources & evidence

ORD record
ord-0fdbbd07a0804ef6b5993401cc3d7cda
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

Loading…