Hydrazine hydrate (1:1) → HCID 66755984, compound

HRID 1866816Notes

Reaction equation

HRID 1866816 reaction equation
[CH2:1]([CH:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[O:10][CH:9]1[C@H:20]([N:24]1[CH:28]=[C:27]([CH2:29][N:30]2C(=O)C3=CC=CC=C3C2=O)[N:26]=[C:25]1[C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CCO>[NH2:30][CH2:29][C:27]1[N:26]=[C:25]([C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)[N:24]([C@@H:20]([C:9]2[O:10][C:11]3[C:16]([C:17](=[O:18])[C:8]=2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:15][CH:14]=[C:13]([Cl:19])[CH:12]=3)[CH:21]([CH3:23])[CH3:22])[CH:28]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66755951HCID 66755951, compound

Product 1

HCID 66755984HCID 66755984, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To N-{1-[(R)-1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-chromen-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-ylmethyl}-phthalimide (0.50 g, 0.78 mMol) in EtOH (15 mL) was added hydrazine monohydrate (0.12 mL, 2.5 mMol). The reaction was stirred at RT for 72 h, filtered through a pad of Celite® to remove the insoluble precipitate, rinsed with EtOH and evaporated to dryness. Purification by flash chromatography on silica gel [5-10% (5% NH4OH in MeOH)/CH2Cl2] gave the title compound (364 mg, 91%) as a white solid foam: 1H NMR (400 MHz, CDCl3) δ 8.14 (d, J=8.6 Hz, 1H), 7.63 (d. J=1.8 Hz, 1H), 7.37 (m, 6H), 7.15 (m, 3H), 6.71 (d, J=1.7 Hz, 1H), 6.69 (s, 1H), 5.00 (d, 0.1=10.9 Hz, 1H), 4.07 (d, J=15.5 Hz, 1H), 3.92 (d, 1H), 3.88 (d, 1H), 2.72 (br s, 2H), 2.65 (m, 1H), 2.49 (s, 3H), 2.48 (d, J=15.5 Hz, 1H), 0.93 (d, J=6.6 Hz, 3H), 0.30 (d, J=6.7 Hz, 3H); MS (ES) m/e 512.2 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. customto remove the insoluble precipitate
  3. washrinsed with EtOH
  4. customevaporated to dryness
  5. customPurification by flash chromatography on silica gel [5-10% (5% NH4OH in MeOH)/CH2Cl2]

Sources & evidence

ORD record
ord-eee341c62d3748a390d4598b57426ad5
Source dataset
uspto-grants-2009_12
Patent number
US07629477B2

Reaction notes

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