6-cyano-1H-indole-2-carboxylic Acid → HCID 178451371, compound

HRID 1291022Notes

Reaction equation

HRID 1291022 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([OH:14])=O)[NH:9]2)=[CH:5][CH:4]=1)#[N:2].[NH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([O:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:17]1>>[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([NH:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([O:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:17]3)=[O:14])[NH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 105836876-cyano-1H-indole-2-carboxylic AcidHCID 178451370HCID 178451370, compound

Product 1

HCID 178451371HCID 178451371, compoundYield 89.3%

Procedure

In the same manner as in Example 1 (2), 6-cyano-2-indolecarboxylic acid (244 mg, 1.31 mmol) and t-butyl trans-(4-aminocyclohexyloxy)acetate (300 mg, 1.31 mmol) were condensed. The reaction mixture was purified by silica gel column chromatography (chloroform/methanol=50/1-1/1) to give 465 mg of t-butyl trans-[4-[(6-cyano-2-indolyl)carbonylamino]cyclohexyloxy]acetate as a brown solid (89%).

Workup

  1. customcondensed
  2. customThe reaction mixture was purified by silica gel column chromatography (chloroform/methanol=50/1-1/1)

Sources & evidence

ORD record
ord-f6514cc40fe147729da92ab4030ddc87
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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