Ammonium Chloride → HCID 59825732, compound

HRID 1696651Notes

Reaction equation

HRID 1696651 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[O:15][C:14]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][C:22]([CH3:28])([CH3:27])[CH2:21][C:20]=3[NH:19][C:18]3=[C:29]([C:32](O)=[O:33])[NH:30][CH:31]=[C:17]23)=[CH:13][CH:12]=1.C[N:36](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[NH4+].C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[O:15][C:14]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][C:22]([CH3:27])([CH3:28])[CH2:21][C:20]=3[NH:19][C:18]3=[C:29]([C:32]([NH2:36])=[O:33])[NH:30][CH:31]=[C:17]23)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59825635HCID 59825635, compound

Product 1

HCID 59825732HCID 59825732, compoundYield 14.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 60 mg (0.126 mmol) of 9-[5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-6.6 dimethyl-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid in 2 ml dimethylformamide was added successively 72 mg (0.189 mmol) of HBTU, 14 mg (0.253 mmol) of ammonium chloride, 74 mg (0.574 mmol) of N,N-diisopropylethylamine in a round bottom flask. The reaction mixture was stirred overnight at room temperature. Water was then added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried on magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The residue was purified by preparative LCMS (method C) giving 8.9 mg of 9-[5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-6,6-dimethyl-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxamide (12% yield). Analytical LC/MS method B: [M+H]+=474.5; retention time: 2.90 min; 70% UV (DAD) purity.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was purified by preparative LCMS (method C)

Sources & evidence

ORD record
ord-d86153bad9b249c6bcad0bd3ff10c178
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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