1-Hydroxybenzotriazole → HCID 86603103, compound

HRID 855418Notes

Reaction equation

HRID 855418 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C1C=CC2N(O)N=NC=2C=1.[C:24]([C:28]1[CH:44]=[CH:43][C:31]([CH2:32][NH:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:24]([C:28]1[CH:44]=[CH:43][C:31]([CH2:32][N:33]([CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[C:11]([C:8]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]3[C:7]=2[NH:6][CH:5]=[CH:4]3)=[O:13])=[CH:30][CH:29]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 29280418(4-Tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amineHCID 693468504-Chloro-1H-indole-7-carboxylic acid

Product 1

HCID 86603103HCID 86603103, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 64 mg (0.33 mmol) of 4-chloro-1H-indole-7-carboxylic acid in 2 ml DCM 50 mg of HOBT (0.33 mmol) were added and the reaction mixture was stirred for 15 min at rt under nitrogen. 85 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amine in 1 ml DCM were added and then 63 mg (0.33 mmol) of EDC.HCl. The reaction mixture was stirred over night at rt to yield a slight turbid yellow solution. The solvent was evaporated and the residue was dissolved in 1,2-dichloro ethane. The reaction mixture was stirred at reflux for 3 h. The solvent was evaporated and the residue was purified by column chromatography (25 g silica gel, heptane/EtOAc 7:3) to yield 90 mg (65%) product as a light yellow viscous oil. MS (ISP) 463.4 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred over night at rt
  2. customto yield a slight turbid yellow solution
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in 1,2-dichloro ethane
  5. stirringThe reaction mixture was stirred
  6. temperatureat reflux for 3 h
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography (25 g silica gel, heptane/EtOAc 7:3)

Sources & evidence

ORD record
ord-fa923246e7d54064af09f388dd795d99
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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