Dimethylformamide → HCID 67436034, compound

HRID 1663020Notes

Reaction equation

HRID 1663020 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:25])[CH:12]2[CH2:20][CH2:19][C:18]3[NH:17][C:16]4[CH:21]=[CH:22][CH:23]=[N:24][C:15]=4[C:14]=3[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CN(C=O)C.[H-].[Na+].[C:33]([O:37][C:38](=[O:41])[CH2:39]Br)([CH3:36])([CH3:35])[CH3:34]>CO>[C:33]([O:37][C:38](=[O:41])[CH2:39][N:17]1[C:18]2[CH2:19][CH2:20][CH:12]([N:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH3:25])[CH2:13][C:14]=2[C:15]2[N:24]=[CH:23][CH:22]=[CH:21][C:16]1=2)([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 67436254HCID 67436254, compound

Product 1

HCID 67436034HCID 67436034, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-fluoro-N-methyl-N-(6,7,8,9-tetrahydro-5H-pyrido[3,2-b]indol-8-yl)-benzenesulfonamide (2.8 g, 7.8 mmol) and DMF (22 mL) was cooled to 0° C. Sodium hydride (340 mg, 8.6 mmol, 60% dispersion in mineral oil) was added at 0° C. and after 30 min, tert-butylbromoacetate (1.3 mL, 8.9 mmol) was added at 0° C. After 1 hour, MeOH was added and the reaction mixture was filtered. The organic layer was concentrated and the residue purified by reverse phase preparative HPLC to afford 700 mg of {8-[(4-fluoro-benzenesulfonyl)-methyl-amino]-6,7,8,9-tetrahydro-pyrido[3,2-b]indol-5-yl}-acetic acid tert-butyl ester. Mass spectrometric data [M+H]+=474.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationThe organic layer was concentrated
  3. customthe residue purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-96d4224478fb4959bfe50cec541e4e77
Source dataset
uspto-grants-2011_10
Patent number
US08034826B2

Reaction notes

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