Hydrochloric Acid → HCID 18355367, compound

HRID 429683Notes

Reaction equation

HRID 429683 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[C:12]([C:17]([NH:19][C:20]3[CH:51]=[CH:50][C:23]([C:24]([N:26]([CH3:49])[C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=4[O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([N:42]4[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]4)=[O:41])=[O:25])=[CH:22][C:21]=3[O:52][CH3:53])=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:54][O:55][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)=O)(C)(C)C.Cl>[OH-].[Na+].CO>[OH:55][CH2:54][C:9]1[NH:8][C:16]2[C:11]([CH:10]=1)=[C:12]([C:17]([NH:19][C:20]1[CH:51]=[CH:50][C:23]([C:24]([N:26]([CH3:49])[C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=3[O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([N:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)=[O:41])=[O:25])=[CH:22][C:21]=1[O:52][CH3:53])=[O:18])[CH:13]=[CH:14][CH:15]=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18354880HCID 18354880, compound

Product 1

HCID 18355367HCID 18355367, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The solution of 4-[(1-tert-butoxycarbonyl-2-tert-butyldiphenylsilyloxymethylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (615 mg) in 1N sodium hydroxide aqueous solution (3.1 ml) and methanol (10 ml) was stirred at ambient temperature overnight. The resulting solution was neutralized with 1N hydrochloric acid and extracted with ethyl acetate (20 ml). The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; 8-10% methanol in chloroform) to give 4-[(2-hydroxymethylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (362 mg).

Workup

  1. extractionextracted with ethyl acetate (20 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent; 8-10% methanol in chloroform)

Sources & evidence

ORD record
ord-49683b1c06524e568b6d32dab0d7de02
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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