HCID 507868, compound → HCID 59067903, compound

HRID 2416664Notes

Reaction equation

HRID 2416664 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:32])=[C:9]2[C:13]=1[NH:12][CH:11]=[C:10]2[C:14](=[O:31])[C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18]1)=[O:16])=[O:4].[BH4-].[Na+]>C(O)C>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:32])=[C:9]2[C:13]=1[NH:12][CH:11]=[C:10]2[CH:14]([OH:31])[C:15]([N:17]1[CH2:18][CH2:19][N:20]([C:23](=[O:30])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:21][CH2:22]1)=[O:16])=[O:4]

Participants

4

Reactant 2

HCID 507868HCID 507868, compoundHCID 4311764Sodium borohydride

Product 1

HCID 59067903HCID 59067903, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3-[2-(4-Benzoyl-piperazin-1-yl)-2-oxo-acetyl]-4-fluoro-1H-indole-7-carboxylic acid methylamide (A″′, 0.260 g., 0.60 mmol) in absolute ethanol (5 mL) under nitrogen atmosphere was treated with sodium borohydride (0.031 g, 0.8 mmol). The suspension became a solution within several minutes. The reaction was stirred overnight. Solvent was removed in-vaccuo and the residue was purified by silica gel column chromatography, eluting with ethyl acetate:methanol (100:0 changing to 90:10). Product fractions were pooled and dried in-vaccuo to give the title compound (Example 32, 0.106 g, 0.24 mmol, Y 40%). 1H—NMR (300 MHz, d-6 DMSO): 11.33 (s, 1H indole NH); 8.51 (d, 1H, CONH); 7.7-7.1 (m, 7H, aromatic); 6.85 (m, 1H, C5-H); 5.70 (b, 1H, OH); 5.27 (d, 1H, CHCO); 3.8-3.3 (2×br, 8H, piperazine)2.83 (d, 3H, CH3). LRMS (ES+) m/z [M+Na]+=460.9, (ES−) [M−H]−=437.0.

Workup

  1. customwithin several minutes
  2. customSolvent was removed in-vaccuo and the residue
  3. customwas purified by silica gel column chromatography
  4. washeluting with ethyl acetate:methanol (100:0 changing to 90:10)
  5. customdried in-vaccuo

Sources & evidence

ORD record
ord-b64587cfe1dd47cb81f03a8e47211ad1
Source dataset
uspto-grants-2004_11
Patent number
US06825201B2

Reaction notes

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