Benzylamine → HCID 135774181, compound

HRID 2375123Notes

Reaction equation

HRID 2375123 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:24](=[O:25])[NH:23][N:22]=[CH:21][C:10]3=[C:11]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)[NH:12][C:13]([CH:14]=1)=[C:9]23)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:32]([NH2:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[CH2:32]([NH:39][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:24](=[O:25])[NH:23][N:22]=[CH:21][C:10]3=[C:11]([C:15]4[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=4)[NH:12][C:13]([CH:14]=1)=[C:9]23)=[O:4])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 136141710HCID 136141710, compound

Product 1

HCID 135774181HCID 135774181, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-Chloro-N-[2-(1-methyl-1H-pyrazol-4-yl)-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl]-acetamide 270(a) (100 mg, 0.28 mmol) in DMF (1.5 mL) was added Cs2CO3 (˜5 eq.) followed by benzyl amine (33 mg, 0.3 mmol.). The resulting mixture was heated at 50° C. overnight. Excess Cs2CO3 was filtered and the clear dark solution was purified by reverse phase HPLC to afford 15 mg of desired product as yellow solids.

Workup

  1. filtrationExcess Cs2CO3 was filtered
  2. customthe clear dark solution was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-9fccb2174a83450eb1d7e5bb48cf8c07
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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