Isobutylamine → HCID 67535969, compound

HRID 2383055Notes

Reaction equation

HRID 2383055 reaction equation
[CH:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=3)[CH2:10][CH2:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:53][CH:54]([CH3:57])[CH2:55][NH2:56]>C(Cl)Cl.O>[CH:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH:56][CH2:55][CH:54]([CH3:57])[CH3:53])=[O:19])[CH:15]=3)[CH2:10][CH2:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59396297HCID 59396297, compound

Product 1

HCID 67535969HCID 67535969, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-cyclohexyl-3,4-dihydroisoquinoline-7-carboxylic acid (1.15 g) was dissolved in methylene chloride (15 mL). O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (2.03 g), N,N-diisopropylethylamine (1.55 mL), and 2-methyl-1-propanamine (0.87 mL) were added thereto, followed by stirring at room temperature for 18 hours. Then, water was added to the mixture, followed by extraction with chloroform. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain 1-cyclohexyl-N-isobutyl-3,4-dihydroisoquinoline-7-carboxamide (700 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record
ord-6b9c0f3bfbdf489d9f1c9800a77889a0
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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