Hydrazine hydrate (1:1) → HCID 10006598, compound

HRID 1350635Notes

Reaction equation

HRID 1350635 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C: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:42]=[CH:43][C:44]([CH3:47])=[CH:45][CH:46]=2)[N:24]([C@@H:20]([C:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=3)[N:10]=2)[CH:21]([CH3:23])[CH3:22])[CH:28]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69078040HCID 69078040, compound

Product 1

HCID 10006598HCID 10006598, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To N-{1-[(R)-1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-ylmethyl}-phthalimide (3.50 g, 5.5 mMol) in EtOH (100 mL) was added hydrazine monohydrate (1.1 mL, 22.7 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 (2.71 g, 96%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.24 (d, J=8.6 Hz, 1H), 7.80 (d, J=2.0 Hz, 1H), 7.40–7.51 (m, 6H), 7.15–7.22 (m, 3H), 6.43 (d, J=7.1 Hz, 2H), 5.78 (d, J=16.3 Hz, 1H), 4.84 (d, J=10.5 Hz, 1H), 3.87 (d, J=16.3 Hz, 1H), 3.83 (2d, 2H), 3.00 (m, 1H), 2.60 (br s, 2H), 2.54 (s, 3H), 0.90 (d, J=6.7 Hz, 3H), 0.31 (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-6b0703078a7d4f7aae6d8d6682dc5343
Source dataset
uspto-grants-2007_05
Patent number
US07214800B2

Reaction notes

Loading…