Acetonitrile → Ammonia

HRID 637056Notes

Reaction equation

HRID 637056 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)([CH2:12][CH2:13]OS(C)(=O)=O)[C:8]1=[O:30].I.[CH2:39]([O:41][CH2:42][CH2:43][N:44]1[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2[N:46]=[C:45]1[N:53]1[CH2:59][CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)[CH3:40].C(N(CC)C(C)C)(C)C.C(#N)C>ClCCl.CO.C(OCC)(=O)C>[NH3:7].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:12][CH2:13][N:56]2[CH2:57][CH2:58][CH2:59][N:53]([C:45]3[N:44]([CH2:43][CH2:42][O:41][CH2:39][CH3:40])[C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=4[N:46]=3)[CH2:54][CH2:55]2)([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=2)[C:8]1=[O:30]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 18464575HCID 18464575, compoundHCID 865838874-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl) [1,4]diazepane hydriodic acid salt

Product 2

HCID 222AmmoniaYield 0.5%HCID 18464726HCID 18464726, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(4-(trifluoromethyl)phenylmethyl)-3-(2-methanesulfonyloxyethyl)-2-oxopyrrolidine (0.54 g, 0.99 mmol), 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (0.54 g, 0.99 mmol), and N,N-diisopropylethylamine (0.5 g, 3.94 mmol) and acetonitrile (10 mL). Heat to reflux. After 12 hours, cool to ambient temperature, dilute with dichloromethane and extract twice with water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 0.5% concentrated aqueous ammonia solution/5% methanol/ethyl acetate to give the title compound: Rf=0.34 (silica gel, 0.5% concentrated aqueous ammonia solution/5% methanol/ethyl acetate).

Workup

  1. temperatureHeat to reflux
  2. extractionextract twice with water
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-3ad429911b074f278f2f8c710272bdd4
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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