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Potassium Carbonate → (7R,8R,9R)-3,9-Diphenyl-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 723391
Notes
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Reaction equation

HRID 723391 reaction equation
C([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:23])=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([O:24][CH2:25][CH2:26][O:27][CH3:28])[C@H:6]([O:29]C(=O)C(C)(C)C)[C@H:5]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>NC(O)C>[C:17]1([C:16]2[N:11]3[CH:10]=[CH:9][C:8]4[C@@H:7]([O:24][CH2:25][CH2:26][O:27][CH3:28])[C@H:6]([OH:29])[C@@H:5]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[NH:4][C:13]=4[C:12]3=[N:14][C:15]=2[CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69586312(7R,8R,9R)-10-acetyl-3,9-diphenyl-7-(2-methoxyethoxy)-2-methyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Product 1

HCID 11304956(7R,8R,9R)-3,9-Diphenyl-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Reagents, catalysts & solvents 1

HCID 522583Acetaldehyde ammoniaSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 1.14 g (2.05 mmol) of (7R,8R,9R)-10-acetyl-3,9-diphenyl-7-(2-methoxyethoxy)-2-methyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine and 2.28 g (16.5 mmol) potassium carbonate in aminoethanol is stirred at 60° C. for 4 h. The reaction is quenched by adding of saturated aqueous ammonium chloride solution. Subsequently the mixture is extracted twice with ethyl acetate. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (diethyl ether/petrol ether: 7/3) to give 0.52 g (1.21 mmol/60%) of the title compound as a colourless solid with a melting point of 190–192° C. (diethyl ether).

Workup

  1. customThe reaction is quenched
  2. additionby adding of saturated aqueous ammonium chloride solution
  3. extractionSubsequently the mixture is extracted twice with ethyl acetate
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customThe crude product is purified by column chromatography (diethyl ether/petrol ether: 7/3)

Sources & evidence

ORD record
ord-6abd21351a764ff39d10a9b922d64dda
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07141567B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes