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Acetone → HCID 21477679, compound

HRID 1449753
Notes
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Reaction equation

HRID 1449753 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 176
Acetic Acid
Solvent
HCID 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-91d78764a77b4d7a9a4ff498186d17b2
Source dataset
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05599930

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes