Piperidine → HCID 69590695, compound

HRID 1795869Notes

Reaction equation

HRID 1795869 reaction equation
C([NH:18][C@H:19]([C:29]([NH:31][C:32]1[CH:50]=[CH:49][C:35]([O:36][C:37]2[CH:38]=[C:39]3[C:43](=[CH:44][CH:45]=2)[NH:42][C:41]([NH2:46])=[C:40]3[C:47]#[N:48])=[CH:34][CH:33]=1)=[O:30])[CH2:20][O:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.N1CCCCC1>C(Cl)(Cl)Cl>[C:25]([O:24][C:22]([O:21][CH2:20][C@@H:19]([C:29]([NH:31][C:32]1[CH:50]=[CH:49][C:35]([O:36][C:37]2[CH:38]=[C:39]3[C:43](=[CH:44][CH:45]=2)[NH:42][C:41]([NH2:46])=[C:40]3[C:47]#[N:48])=[CH:34][CH:33]=1)=[O:30])[NH2:18])=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 69590405HCID 69590405, compound

Product 1

HCID 69590695HCID 69590695, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-[4-({N-FMOC-O-t-butoxycarbonylseryl}amino)phenoxy]-2-amino-1H-indole-3-carbonitrile (1.45 g; 2.3 mmol) in CHCl3, (30 ml) was treated dropwise with piperidine (3.25 ml). The mixture was stirred for 3 hours at room temperature and was directly purified by flash chromatography eluting with increasingly polar mixtures of MeOH/CH2Cl2 (2.5 to 10% MeOH). The appropriate fractions were evaporated to give 5-[4-(O-t-butoxycarbonylserylamino)phenoxy]-2-amino-1H-indole-3-carbonitrile as a white solid (878 mg).

Workup

  1. customwas directly purified by flash chromatography
  2. washeluting
  3. temperaturewith increasingly polar mixtures of MeOH/CH2Cl2 (2.5 to 10% MeOH)
  4. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-b16c63f7b99941f0bd67312109557d2d
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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