FD&C Yellow 6 → HCID 136128423, compound

HRID 220971Notes

Reaction equation

HRID 220971 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:30][C:29]3[CH:28]=[N:27][N:26]([CH3:31])[C:25]=3[NH:24][C:23]3[CH:32]=[C:33]([Cl:36])[CH:34]=[CH:35][C:22]2=3)=[O:20])=[CH:15][C:14]=1[F:37].C1C(N=NC2C3C=CC(S([O-])(=O)=O)=CC=3C=CC=2O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+]>C1COCC1>[Cl:36][C:33]1[CH:34]=[CH:35][C:22]2[N:21]([C:19]([C:16]3[CH:17]=[CH:18][C:13]([CH2:12][NH:11][CH2:10][CH2:9][OH:8])=[C:14]([F:37])[CH:15]=3)=[O:20])[CH2:30][C:29]3[CH:28]=[N:27][N:26]([CH3:31])[C:25]=3[NH:24][C:23]=2[CH:32]=1

Participants

5

Reactant 3

HCID 17730FD&C Yellow 6HCID 21226445Aluminium lithium hydrideHCID 136128371HCID 136128371, compound

Product 1

HCID 136128423HCID 136128423, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (14.5 mg, 0.38 mmol) was added to a solution of [4-(6-chloro-3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-fluoro-benzylamino]-acetic acid methyl ester from example E110 (58.5 mg, 0.13 mmol) in THF (5 ml), and the mixture was stirred at room temperature for 30 min. Before being quenched with MeOH and extracted with EtOAc. The organic extract was washed with brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 10% methanol:90% di-chloromethane then 20% methanol:80% dichloromethane) to give a pale yellow solid identified as the title compound (15 mg, 28%).

Workup

  1. customBefore being quenched with MeOH
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluant
  8. custom10% methanol:90% di-chloromethane then 20% methanol:80% dichloromethane) to give a pale yellow solid

Sources & evidence

ORD record
ord-74e1816d8b78419a86965268d8d813f3
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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