5-Benzyloxyindole → HCID 69585959, compound

HRID 2188018Notes

Reaction equation

HRID 2188018 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH2:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:12]([CH2:26][NH2:27])[C:11]=2[S:10][C:9]=1[NH2:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:29]N1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH:51]([N:54]([CH:57]([CH3:59])[CH3:58])CC)([CH3:53])[CH3:52].[CH2:60]([O:67][C:68]1[CH:69]=C2C(=C[CH:76]=1)NC=C2)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C)C=O>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH2:14][N:13]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[CH:12]([CH2:26][NH:27][C:59]([C:57]3[NH:54][C:51]4[C:52]([CH:58]=3)=[CH:69][C:68]([O:67][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[CH:76][CH:53]=4)=[O:29])[C:11]=2[S:10][C:9]=1[NH2:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 146245-BenzyloxyindoleHCID 81531Diisopropylethylamine2×HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219366842-Amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

Product 1

HCID 69585959HCID 69585959, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (0.50 g; 1.2 mmol) was dissolved in N,N-dimethylformamide (20 ml). 1-Hydroxy-7-azabenzotriazole (0.19 g; 1.3 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.26 g; 1.3 mmol) and diisopropyl-ethylamine (0.23 ml; 1.3 mmol) were added and the mixture was stirred for 15 min. 5-Benzyloxyindole (0.36 g; 1.3 mmol) was dissolved in N,N-dimethylformamide (20 ml) and added. Diisopropylethylamine (0.23 ml; 1.3 mmol) was added and the mixture was stirred overnight. The solvent was removed in vacuo, the residue dissolved in dichloromethane (30 ml) and the organic phase washed with an aqueous solution of sodium hydrogencarbonate (15 ml). The organic phase was dried (MgSO4), filtered and the solvent removed in vacuo. The residue was chromatographed on silica using ethyl acetate/heptane (1:1) as eluent affording 569 mg of 2-amino-7-(((5-benzyloxy-1H-indole-2-carbonyl)amino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an oil.

Workup

  1. additionadded
  2. stirringthe mixture was stirred overnight
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in dichloromethane (30 ml)
  5. washthe organic phase washed with an aqueous solution of sodium hydrogencarbonate (15 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-bcf63c4d2bc547e59aa0357ae4c4f393
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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