1H-Indole-5-Carboxylic Acid → HCID 14985999, compound

HRID 1086855Notes

Reaction equation

HRID 1086855 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:13][S:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=1)(=[O:16])=[O:15]>>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:29]3[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][C:21]4[CH:20]=[CH:19][C:18]([NH:17][S:14]([CH3:13])(=[O:15])=[O:16])=[CH:23][CH:22]=4)[CH2:27][CH2:28]3)=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

3

Reactant 2

HCID 742801H-Indole-5-Carboxylic AcidHCID 14985998HCID 14985998, compound

Product 1

HCID 14985999HCID 14985999, compound

Procedure

In the manner described in Example 24, indole-5-carboxylic acid (100 mg, 0.62 mmol) and 1-[2-(4-methanesulfonamidophenyl)ethyl]piperazine (180 mg, 0.64 mmol) gave, after purification by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 ; 95:5:0.5 and trituration with hexane/EtOAc, the piperazine (68 mg, 26%), mp 94°-97° C. Elemental analysis for C22H26N4O3S.0.5H2O: Calculated: C, 60.66; H, 6.26; N, 12.86%. Found: C, 61.02; H, 6.19; N, 12.51%.

Workup

  1. customgave
  2. customafter purification by flash column chromatography on silica gel
  3. washeluting with CH2Cl2 /MeOH/NH3

Sources & evidence

ORD record
ord-6598347175664b66b8deaebdedc5b27b
Source dataset
uspto-grants-1991_07
Patent number
US05032598

Reaction notes

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