Acetone → HCID 21477679, compound

HRID 2293784Notes

Reaction equation

HRID 2293784 reaction equation
[N:1]1([C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27]4[C:32]([NH:33][CH:34]([CH3:36])[CH3:35])=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:23][CH2:22]2)=[O:20])=[CH:13]3)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+].[CH3:41][C:42]([CH3:44])=O.[OH-].[Na+]>CO.C(O)(=O)C>[CH3:41][CH:42]([N:4]1[CH2:3][CH2:2][N:1]([C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([C:19]([N:21]2[CH2:22][CH2:23][N:24]([C:27]4[C:32]([NH:33][CH:34]([CH3:36])[CH3:35])=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:25][CH2:26]2)=[O:20])=[CH:13]3)=[O:8])[CH2:6][CH2:5]1)[CH3:44]

Participants

7

Reactant 4

HCID 180Acetone2×HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2×HCID 21477598HCID 21477598, compound

Product 1

HCID 21477679HCID 21477679, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-[5-(1-piperazinylcarbonylamino)-indole-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine (EXAMPLE 46, 0.41 g) in methanol (50 ml) is added sodium cyanoborohydride (53 mg) and acetone (1 ml). Additional sodium cyanoborohydride (44.3 mg total) and excess acetone are added in portions until the reaction is complete as judged by TLC on silica gel. The mixture is acidified with acetic acid, neutralized with 50% aqueous sodium hydroxide and concentrated. The residue is dissolved in methylene chloride, washed with water, saturated potassium carbonate solution, and saline and dried over sodium sulfate followed by concentration. The resulting material is purified by chromatography on silica gel (100 ml) packed in methanol/chloroform (1/99) and eluted with a methanol/chloroform gradient (1→5%) to give the title compound, NMR (chloroform-d) 9.14, 7.71, 7.33, 7.17, 6.95, 6.86, 6.74, 4.06, 3.58, 3.20, 2.78, 2.60, 1.27, 1.08 δ.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washwashed with water, saturated potassium carbonate solution, and saline
  4. dry with materialdried over sodium sulfate
  5. concentrationfollowed by concentration
  6. customThe resulting material is purified by chromatography on silica gel (100 ml)
  7. washeluted with a methanol/chloroform gradient (1→5%)

Sources & evidence

ORD record
ord-b7197a7c520e490785b9889f5661013f
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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