Ethylenediamine → N-(3,4-Difluorobenzyl)-2-(4,5-dihydro-1H-imidazol-2-yl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

HRID 40106Notes

Reaction equation

HRID 40106 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[CH:29]=O)=[O:8].[CH2:35]([NH2:38])[CH2:36][NH2:37].C1C(=O)N(Br)C(=O)C1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:20])[CH3:21])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[C:29]1[NH:37][CH2:36][CH2:35][N:38]=1)=[O:8]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 67184N-bromobutanimideHCID 59762313HCID 59762313, compound2×

Product 1

HCID 59762307N-(3,4-Difluorobenzyl)-2-(4,5-dihydro-1H-imidazol-2-yl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3,4-difluorobenzyl)-2-formyl-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide (Compound 105, 27 mg, 0.058 mmol) in CH2Cl2 (2 ml) was added 1,2-ethylene-diamine (5 μl, 0.070 mmol). The reaction was stirred at room temperature for 1 h and NBS (13 mg, 0.070 mmol) was added. The reaction was stirred for 16 h and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel (9:1 EtOAc-Et3N, then 8:2:1 EtOAc-MeOH-Et3N) followed by PTLC eluted with EtOAc to yield the title compound.

Workup

  1. stirringThe reaction was stirred for 16 h
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by chromatography on silica gel (9:1 EtOAc-Et3N
  4. washeluted with EtOAc

Sources & evidence

ORD record
ord-aca7d67b53214ed7ad76bd4b06e6972f
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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