Hydrazine → HCID 11661655, compound

HRID 1178851Notes

Reaction equation

[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][O:7][CH2:8][C@:9]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:13][CH2:12][C@@H:11]([N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:10]1.NN>C1(C)C=CC=CC=1>[F:1][C:2]([F:38])([F:39])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][O:7][CH2:8][C@:9]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:13][CH2:12][C@@H:11]([NH2:14])[CH2:10]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-((1R,3R)-3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclopentyl)isoindoline-1,3-dione (68 mg), available from Example 7, in toluene (0.50 mL) was added anhydrous hydrazine (41 μL), and the reaction mixture was heated at 80° C. for 12 h. The precipitate was removed by filtration, and the filtrate was evaporated in vacuo to give the title compound (49 mg). 1H NMR (CDCl3, 400 MHz) δ 1.46 (1H, m), 1.60 (2H, broad s), 1.74 (1H, dd, J=6.0, 12.8 Hz), 2.09 (2H, m), 2.19 (1H, m), 2.48 (1H, dd, J=6.8, 12.8 Hz), 3.40 (1H, d, J=8.8 Hz), 3.44 (1H, d, J=8.8 Hz), 3.53 (1H, quintet, J=7.2 Hz), 4.43 (2H, s), 7.25 (5H, m), 7.55 (2H, s), and 7.73 (1H, s). HRMS m/z calcd for C21H22F6NO (M+H)+ 418.1607. found 546.1621.

Workup

customThe precipitate was removed by filtration
customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record: ord-bfa3c3c6a9964fa1995d69056ce77113
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276631B2

Reaction notes

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