Hydrazine → HCID 42602280, compound

HRID 1867651Notes

Reaction equation

[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:19][CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][O:10]1.NN>C(O)C.C(OCC)C>[F:37][C:35]([F:36])([F:38])[C:33]1[CH:32]=[C:5]([CH:4]=[C:3]([C:2]([F:40])([F:39])[F:1])[CH:34]=1)[CH2:6][O:7][CH2:8][C:9]1([CH2:19][CH2:20][NH2:21])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][O:10]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-(2-(1-((3,5-bis(trifluoromethyl)benzyloxy)methyl)isochroman-1-yl)ethyl)isoindoline-1,3-dione (100 mg, 0.177 mmol) in ethanol (1 mL) at room temperature was added hydrazine (0.039 mL, 1.24 mmol). The flask was sealed, heated to 45° C., and held there for 3 h. The reaction was cooled to room temperature, diluted with diethyl ether, and filtered to remove the precipitate which was discarded. The mother liquor was concentrated to give 78 mg (quant.) as a colorless oil. 1H-NMR (CDCl3, 300 MHz) δ 7.75 (s, 1H), 7.69 (s, 2H), 7.05-7.20 (m, 2H), 4.64 (qAB, JAB=13.1 Hz, 2H), 3.99 (m, 2H), 3.71 (qAB, JAB=10.1 Hz, 2H), 2.91 (m, 1H), 2.76 (m, 1H), 2.68 (m, 1H), 2.50 (m, 1H), 2.16 (m, 1H), 2.02 (m, 1H), 1.79 (bs, 2H); 13C-NMR (CDCl3, 126 MHz) δ 141.3, 137.3, 135.0, 131.7 (q, J=33.6 Hz), 129.1, 127.3, 126.8, 126.5, 125.6, 123.4 (q, J=273 Hz), 121.5, 78.4, 76.7, 72.1, 60.7, 41.9, 37.3, 29.6. Mass spec.: 434.37 (MH)+. Accurate mass spec.: m/z 434.1547 [MH]+, Δ=1.8 ppm.

Workup

customThe flask was sealed
temperatureThe reaction was cooled to room temperature
filtrationfiltered
customto remove the precipitate which
concentrationThe mother liquor was concentrated
customto give 78 mg (quant.) as a colorless oil

Sources & evidence

ORD record: ord-23dc267a7f2f4e37970d4d43edf23940
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632861B2

Reaction notes

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