Hydrazine → HCID 58467980, compound

HRID 1879387Notes

Reaction equation

HRID 1879387 reaction equation
NN.[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:21][CH2:20][C@@H:19]([N:22]2C(=O)C3C(=CC=CC=3)C2=O)[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C@H:12]1[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37]>CO>[NH2:22][C@H:19]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C@@H:12]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C@H:11]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([F:10])[C:4]=2[F:3])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58467996HCID 58467996, compound

Product 1

HCID 58467980HCID 58467980, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of hydrazine (1 mL, 31.9 mmol) and tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(1,3-dioxoisoindolin-2-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (0.428 g, 0.823 mmol) in methanol (5 mL) was heated using an oil bath (70° C.) for 4 h. LCMS showed no starting material remaining. The solvent was removed via vacuum and the crude residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried (sodium sulfate), filtered and concentrated. Flash chromatography using methanol in methylene chloride from 0 to 10% gave the desired product (164 mg, 51%): MS(ESI)[M+H+]=390.19; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.46 (1H, d, J=4.0 Hz), 7.63 (1H, d, J=7.5 Hz), 7.18 (1H, dd, J=7.7, 4.9 Hz), 6.92-7.08 (3H, m), 5.24 (1H, t, J=8.8 Hz), 4.50 (1H, dd, J=9.3, 2.5 Hz), 3.18 (1H, br. s.), 2.83 (2H, br. s.), 2.04-2.24 (3H, m), 1.57 (1H, d, J=9.0 Hz), 1.31 (9H, s), 0.68-0.92 (1H, m).

Workup

  1. temperaturewas heated
  2. custom(70° C.)
  3. customfor 4 h
  4. customThe solvent was removed via vacuum
  5. customthe crude residue was partitioned between ethyl acetate and water
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-75e29ea535b44d9989bc3bc0d1c6ee8c
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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