Hydrazine → HCID 58459803, compound

HRID 455000Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C@H:13]([NH:27][C:28]([C@H:30]1[CH2:32][C@@H:31]1[C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)=[O:29])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]([CH3:25])[CH2:23][CH3:24])=[CH:16][C:15]=1[CH3:26].NN>CCO>[NH2:3][CH2:12][C@H:13]([NH:27][C:28]([C@H:30]1[CH2:32][C@@H:31]1[C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)=[O:29])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]([CH3:25])[CH2:23][CH3:24])=[CH:16][C:15]=1[CH3:26]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of (1S,2S)-2-Thiophen-2-yl-cyclopropanecarboxylic acid {(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-[2-methyl-4-((S)-2-methyl-butoxy)-phenyl]-ethyl}-amide (50 mg, 0.097 mmol) dissolved in 5 mL EtOH was added anhydrous hydrazine (31 mg, 0.97 mmol), and heated to 55° C. for 1 hr with stirring. The reaction mixture was concentrated on the rotavap, and the residue redissolved in EtOAc, and washed with aq. NaHCO3, brine and dried over MgSO4. It was concentrated and purified on the neutral PREP HPLC to obtain 19 mg (51%) of the product. 1H NMR (400 MHz, MeOD) δ ppm 8.73-8.68 (d, J=5.2 Hz, 1H), 7.23-7.31 (m, 1H), 7.16 (dd, J=5.1, 1.3 Hz, 1H), 6.89 (dd, J=5.2, 3.4 Hz, 1H), 6.82 (dd, J=4.7, 2.1 Hz, 3H), 5.36-5.48 (m, 1H), 3.68-3.89 (m, 2H), 3.33-3.29 (m, 2H), 2.51-2.60 (m, 1H), 2.40 (s, 3H), 1.98 (d, J=3.7 Hz, 1H), 1.77-1.87 (m, 1H), 1.54-1.66 (m, 2H), 1.23-1.33 (m, 2H), 1.02 (d, 3H), 0.97 (d, J=6.8 Hz, 3H); m/e LCMS calcd 387.3 [(M+1)+, for C22H31N2O2S 387.3].

Workup

concentrationThe reaction mixture was concentrated on the rotavap
dissolutionthe residue redissolved in EtOAc
washwashed with aq. NaHCO3, brine
dry with materialdried over MgSO4
concentrationIt was concentrated
custompurified on the neutral PREP HPLC

Sources & evidence

ORD record: ord-0fba9d44256e4cb889ad52e22fefabff
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497271B2

Reaction notes

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