Methanol → HCID 136141735, compound

HRID 2375111Notes

Reaction equation

HRID 2375111 reaction equation
[Cl:1]N1C(=O)CCC1=O.COC([C:13]1[NH:14][C:15]2[CH:16]=[C:17]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:18]=[C:19]3[C:25](=[O:26])[NH:24][N:23]=[CH:22][C:21]=1[C:20]=23)=O.CO.C(OCC)(=O)C>CN(C)C=O.C(Cl)(Cl)Cl>[C:31]([O:30][C:28](=[O:29])[NH:27][C:17]1[CH:18]=[C:19]2[C:25](=[O:26])[NH:24][N:23]=[CH:22][C:21]3=[C:13]([Cl:1])[NH:14][C:15]([CH:16]=1)=[C:20]23)([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 1361816128-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester

Product 1

HCID 136141735HCID 136141735, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

N-Chlorosuccinimide (0.47 g, 3.52 mmol) was added to a solution of Intermediate 147(c) of Example 147 (1.00 g, 3.33 mmol) in anhydrous N,N-dimethylformamide (10 ml) and anhydrous chloroform (6.5 mL). The reaction was heated at 50° C. for 3 hours at which point the volatile components were removed in vacuo. The resulting residue was dissolved in methanol and loaded onto a silica gel plug. The plug was then loaded onto a silica gel column and eluted with 23:2:50 dichloromethane:methanol:ethyl acetate to afford the title compound (1 g, 2.99 mmol) as a yellow solid in 90% yield.

Workup

  1. customwere removed in vacuo
  2. dissolutionThe resulting residue was dissolved in methanol
  3. washeluted with 23:2:50 dichloromethane

Sources & evidence

ORD record
ord-d99cb159c05f4e4f91d0e18b161b7586
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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