Sodium Carbonate → HCID 15228557, compound

HRID 1609481Notes

Reaction equation

HRID 1609481 reaction equation
[CH3:1][N:2]([CH3:40])[C:3]([C@H:5]1[N:10]([C:11](=[O:25])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C:8]2[N:26]=[CH:27][N:28]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[C:32]([CH3:39])[CH:31]=3)[C:7]=2[CH2:6]1)=[O:4].O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.CO>[NH2:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][N:28]2[C:7]3[CH2:6][C@@H:5]([C:3]([N:2]([CH3:40])[CH3:1])=[O:4])[N:10]([C:11](=[O:25])[CH:12]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:9][C:8]=3[N:26]=[CH:27]2)=[CH:31][C:32]=1[CH3:39]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 15228559HCID 15228559, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 15228557HCID 15228557, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-N,N-dimethyl-5-diphenylacetyl-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxamide (III-2) (2.3636 g, 0.00440 mol) was dissolved in a mixture of 28 ml of ethyl acetate and 5 ml of methanol, followed by addition of tin chloride dihydrate (4.9580 g, 0.0220 mol) and agitation of the solution on an 80° C. oil bath in a stream of nitrogen for 30 minutes. The reaction mixture was cooled, neutralized by adding a 5% sodium carbonate solution, and concentrated. The residue was extracted with chloroform. The chloroform layer was washed with water, dried over sodium sulfate, and then concentrated to obtain a light-yellow foamy material (2.2368 g). This material was purified by silica gel column chromatography (Kieselgel 60, 120 g, chloroform methanol=50/1) to obtain the objective compound (II-2) (2.0077 g; yield: 90.0%) as a white foamy material. MS (EI): 508 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. extractionThe residue was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8300fad130e1408f8cd18ebb7b4d84e8
Source dataset
uspto-grants-1995_03
Patent number
US05401736

Reaction notes

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