Potassium Carbonate → HCID 9969332, compound

HRID 723389Notes

Reaction equation

HRID 723389 reaction equation
C([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:19])=[C:16]([CH2:17][OH:18])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([O:20][CH2:21][CH2:22][OH:23])[C@H:6]([O:24]C(=O)C(C)(C)C)[C@H:5]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>NC(O)C>[OH:18][CH2:17][C:16]1[N:11]2[CH:10]=[CH:9][C:8]3[C@@H:7]([O:20][CH2:21][CH2:22][OH:23])[C@H:6]([OH:24])[C@@H:5]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[NH:4][C:13]=3[C:12]2=[N:14][C:15]=1[CH3:19]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69586417HCID 69586417, compound

Product 1

HCID 9969332HCID 9969332, compound

Reagents, catalysts & solvents 1

HCID 522583Acetaldehyde ammoniaSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 0.17 g (0.30 mmol) (7R,8R,9R)-10-acetyl-3-hydroxymethyl-7-(2-hydroxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine and 0.30 g (2.10 mmol) potassium carbonate in aminoethanol is stirred at 90° C. for 2 h. The reaction is quenched by adding the mixture directly of silica gel for purification by column chromatography (dichloromethane/methanol: 13/1) to give 0.02 g (0.06 mmol/19%) of the title compound as a armorph solid. 1H-NMR (200 MHz, [D6] DMSO): δ=2.29 (s, 1H), 3.30–3.44 (m, 2H), 3.46–3.65 (m, 2H), 4.01 (q, 1H), 4.47 (t, 2 H), 4.70 (d, 2H), 6.79 (d, 1H), 7.20–7.43 (m, 5H), 7.63 (d, 1H).

Workup

  1. customThe reaction is quenched
  2. additionby adding the mixture directly of silica gel
  3. customfor purification by column chromatography (dichloromethane/methanol: 13/1)

Sources & evidence

ORD record
ord-c8a71ae90b96408bb8d10f3748b4d8d8
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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